Transition-Metal-Catalyzed Deuteration via Hydrogen Isotope Exchange

Zhi-Jiang Jiang; Jian-Fei Bai; Zhanghua Gao

doi:10.1055/a-2460-7378

SynOpen, Table of Contents

CC BY 4.0 · SynOpen 2024; 08(04): 328-359
DOI: 10.1055/a-2460-7378

graphical review

Transition-Metal-Catalyzed Deuteration via Hydrogen Isotope Exchange

Zhi-Jiang Jiang ∗

^aNingboTech-Cuiying Joint Laboratory of Stable Isotope Technology, School of Biological and Chemical Engineering, NingboTech University, Ningbo, 315100, P. R. of China

,

Jian-Fei Bai

^aNingboTech-Cuiying Joint Laboratory of Stable Isotope Technology, School of Biological and Chemical Engineering, NingboTech University, Ningbo, 315100, P. R. of China

,

Zhanghua Gao ∗

^aNingboTech-Cuiying Joint Laboratory of Stable Isotope Technology, School of Biological and Chemical Engineering, NingboTech University, Ningbo, 315100, P. R. of China

^bNingbo Cuiying Chemical Technology Co. Ltd., Ningbo, 315100, P. R. of China

› Author Affiliations

Abstract

All articles of this category

Abstract

Direct hydrogen isotope exchange represents a distinctive strategy for deuterium labelling, where the protium is directly replaced by deuterium. In this graphical review, we summarize the progress in deuteration via transition-metal-catalyzed hydrogen isotope exchange. The review is organized according to the mechanism of C–H bond activation relating to the homogeneous catalysis, and heterogeneous catalysis is also discussed according to the catalyst type. Representative mechanistic processes are depicted, and proven cases for tritiation are also highlighted.

Key words

H/D exchange - C–H activation - hydrogen-borrowing - deuterium labelling - heavy water - deuterium gas

Full Text

References

References

1a Cargnin S, Serafini M, Pirali T. Future Med. Chem. 2019; 11: 2039
1b Pirali T, Serafini M, Cargnin S, Genazzani AA. J. Med. Chem. 2019; 62: 5276
1c Di Martino RM. C, Maxwell BD, Pirali T. Nat. Rev. Drug Discovery 2023; 22: 562
1d Wang X, Luo Y.-B, Luo Y.-X, Liu M.-C, Lu C.-H, Song R.-J. Appl. Organomet. Chem. 2024; 38: e7602
1e Derdau V, Elmore CS, Hartung T, McKillican B, Mejuch T, Rosenbaum C, Wiebe C. Angew. Chem. Int. Ed. 2023; 62: e202306019

2a Asano H, Elhelaly AE, Hyodo F, Iwasaki R, Noda Y, Kato H, Ichihashi K, Tomita H, Murata M, Mori T, Matsuo M. Clin. Cancer Res. 2023; 29: 5173
2b Chahrour O, Cobice D, Malone J. J. Pharm. Biomed. Anal. 2015; 113: 2
2c Chokkathukalam A, Kim DH, Barrett MP, Breitling R, Creek DJ. Bioanalysis 2014; 6: 511

3a Montenegro E, Ganss S, Bürger M, Correia C, Lackner A, Stolz S, Kröber J, Hayer A, Engelhart J, Linge R, Na W.-K, Na S.-H. SID Symp. Dig. Tech. Pap. 2024; 55: 721
3b Cheng J.-F, Kong F.-C, Zhang K, Cai J.-H, Zhao Y, Wang C.-K, Fan J, Liao L.-S. Chem. Eng. J. 2022; 430: 132822
3c Peng X, Yeh CH, Wang SF, Yan J, Gan S, Su SJ, Zhou X, Zhang YX, Chi Y. Adv. Opt. Mater. 2022; 10: 2201291
3d Bae HJ, Kim JS, Yakubovich A, Jeong J, Park S, Chwae J, Ishibe S, Jung Y, Rai VK, Son WJ, Kim S, Choi H, Baik MH. Adv. Opt. Mater. 2021; 9: 2100630

4a Norcott PL. Chem. Commun. 2022; 58: 2944
4b Kopf S, Bourriquen F, Li W, Neumann H, Junge K, Beller M. Chem. Rev. 2022; 122: 6634
4c Li N, Li Y, Wu X, Zhu C, Xie J. Chem. Soc. Rev. 2022; 51: 6291
4d Zhou R, Ma L, Yang X, Cao J. Org. Chem. Front. 2021; 8: 426
4e Lepron M, Daniel-Bertrand M, Mencia G, Chaudret B, Feuillastre S, Pieters G. Acc. Chem. Res. 2021; 54: 1465
4f Vang ZP, Hintzsche SJ, Clark JR. Chem. Eur. J. 2021; 27: 9988

5a Altus KM, Love JA. Commun. Chem. 2021; 4: 173
5b Dalton T, Faber T, Glorius F. ACS. Cent. Sci. 2021; 7: 245
5c Docherty JH, Lister TM, McArthur G, Findlay MT, Domingo-Legarda P, Kenyon J, Choudhary S, Larrosa I. Chem. Rev. 2023; 123: 7692
5d Rogge T, Kaplaneris N, Chatani N, Kim J, Chang S, Punji B, Schafer LL, Musaev DG, Wencel-Delord J, Roberts CA, Sarpong R, Wilson ZE, Brimble MA, Johansson MJ, Ackermann L. Nat. Rev. Methods Primers 2021; 1: 43

6a Prakash G, Paul N, Oliver GA, Werz DB, Maiti D. Chem. Soc. Rev. 2022; 51: 3123
6b Kang Q.-K, Shi H. Synlett 2021; 33: 329
6c Atzrodt J, Derdau V, Kerr WJ, Reid M. Angew. Chem. Int. Ed. 2018; 57: 3022
6d Atzrodt J, Derdau V, Fey T, Zimmermann J. Angew. Chem. Int. Ed. 2007; 46: 7744

7a Hesk D, Das PR, Evans B. J. Labelled Compd. Radiopharm. 1995; 36: 497
7b Kingston LP, Lockley WJ. S, Mather AN, Spink E, Thompson SP, Wilkinson DJ. Tetrahedron Lett. 2000; 41: 2705
7c Hickey MJ, Jones JR, Kingston LP, Lockley WJ. S, Mather AN, McAuley BM, Wilkinson DJ. Tetrahedron Lett. 2003; 44: 3959
7d McAuley B, Hickey MJ, Kingston LP, Jones JR, Lockley WJ. S, Mather AN, Spink E, Thompson SP, Wilkinson DJ. J. Labelled Compd. Radiopharm. 2003; 46: 1191
7e Garman RN, Hickey MJ, Kingston LP, McAuley B, Jones JR, Lockley WJ. S, Mather AN, Wilkinson DJ. J. Labelled Compd. Radiopharm. 2005; 48: 75
7f Heys R. J. Chem. Soc., Chem. Commun. 1992; 680
7g Heys JR, Shu AY. L, Senderoff SG, Phillips NM. J. Labelled Compd. Radiopharm. 1993; 33: 431
7h Shu AY. L, Chen W, Heys JR. J. Organomet. Chem. 1996; 524: 87
7i Chen W, Garnes KT, Levinson SH, Saunders D, Senderoff SG, Shu AY. L, Villani AJ, Heys JR. J. Labelled Compd. Radiopharm. 1997; 39: 291
7j Shu AY. L, Saunders D, Levinson SH, Landvatter SW, Mahoney A, Senderoff SG, Mack JF, Heys JR. J. Labelled Compd. Radiopharm. 1999; 42: 797
7k Shu AY. L, Heys JR. Tetrahedron Lett. 2000; 41: 9015
7l Ellames GJ, Gibson JS, Herbert JM, McNeill AH. Tetrahedron 2001; 57: 9487
7m Cross PW. C, Ellames GJ, Gibson JS, Herbert JM, Kerr WJ, McNeill AH, Mathers TW. Tetrahedron 2003; 59: 3349
7n Ellames GJ, Gibson JS, Herbert JM, Kerr WJ, McNeill AH. J. Labelled Compd. Radiopharm. 2004; 47: 1
7o Salter R, Bosser I. J. Labelled Compd. Radiopharm. 2003; 46: 489
7p Krüger J, Manmontri B, Fels G. Eur. J. Org. Chem. 2005; 1402

8a Brown JA, Irvine S, Kennedy AR, Kerr WJ, Andersson S, Nilsson GN. Chem. Commun. 2008; 1115
8b Nilsson GN, Kerr WJ. J. Labelled Compd. Radiopharm. 2010; 53: 662
8c Cochrane AR, Irvine S, Kerr WJ, Reid M, Andersson S, Nilsson GN. J. Labelled Compd. Radiopharm. 2013; 56: 451
8d Cross P, Herbert J, Kerr W, McNeill A, Paterson L. Synlett 2015; 27: 111
8e Kerr WJ, Knox GJ, Reid M, Tuttle T. Chem. Sci. 2021; 12: 6747
8f Cochrane AR, Idziak C, Kerr WJ, Mondal B, Paterson LC, Tuttle T, Andersson S, Nilsson GN. Org. Biomol. Chem. 2014; 12: 3598
8g Kennedy AR, Kerr WJ, Moir R, Reid M. Org. Biomol. Chem. 2014; 12: 7927
8h Kerr WJ, Mudd RJ, Owens PK, Reid M, Brown JA, Campos S. J. Labelled Compd. Radiopharm. 2016; 59: 601
8i Brown JA, Cochrane AR, Irvine S, Kerr WJ, Mondal B, Parkinson JA, Paterson LC, Reid M, Tuttle T, Andersson S, Nilsson GN. Adv. Synth. Catal. 2014; 356: 3551
8j Timofeeva DS, Lindsay DM, Kerr WJ, Nelson DJ. Catal. Sci. Technol. 2020; 10: 7249
8k Timofeeva DS, Lindsay DM, Kerr WJ, Nelson DJ. Catal. Sci. Technol. 2021; 11: 5498
8l Morawietz P, Weck R, Scholte AA, Atzrodt J, Güssregen S, Derdau V. Green Chem. 2022; 24: 4824

9a Devlin J, Kerr W, Lindsay D, McCabe T, Reid M, Tuttle T. Molecules 2015; 20: 11676
9b Kerr WJ, Mudd RJ, Paterson LC, Brown JA. Chem. Eur. J. 2014; 20: 14604
9c Valero M, Weck R, Güssregen S, Atzrodt J, Derdau V. Angew. Chem. Int. Ed. 2018; 57: 8159
9d Atzrodt J, Derdau V, Kerr WJ, Reid M, Rojahn P, Weck R. Tetrahedron 2015; 71: 1924
9e Kerr WJ, Lindsay DM, Reid M, Atzrodt J, Derdau V, Rojahn P, Weck R. Chem. Commun. 2016; 52: 6669
9f Kerr WJ, Reid M, Tuttle T. ACS Catal. 2015; 5: 402
9g Kerr WJ, Mudd RJ, Reid M, Atzrodt J, Derdau V. ACS Catal. 2018; 8: 10895
9h Knight NM. L, Thompson JD. F, Parkinson JA, Lindsay DM, Tuttle T, Kerr WJ. Adv. Synth. Catal. 2024; 366: 2577
9i Kerr WJ, Reid M, Tuttle T. Angew. Chem. Int. Ed. 2017; 56: 7808
9j Kerr WJ, Lindsay DM, Owens PK, Reid M, Tuttle T, Campos S. ACS Catal. 2017; 7: 7182
9k Koneczny M, Phong Ho L, Nasr A, Freytag M, Jones PG, Tamm M. Adv. Synth. Catal. 2020; 362: 3857
9l Liu W, Cao L, Zhang Z, Zhang G, Huang S, Huang L, Zhao P, Yan X. Org. Lett. 2020; 22: 2210
9m Zhao L.-L, Wu Y, Huang S, Zhang Z, Liu W, Yan X. Org. Lett. 2021; 23: 9297

10a Parmentier M, Hartung T, Pfaltz A, Muri D. Chem. Eur. J. 2014; 20: 11496
10b Jess K, Derdau V, Weck R, Atzrodt J, Freytag M, Jones PG, Tamm M. Adv. Synth. Catal. 2017; 359: 629
10c Valero M, Burhop A, Jess K, Weck R, Tamm M, Atzrodt J, Derdau V. J. Labelled Compd. Radiopharm. 2018; 61: 380
10d Valero M, Becker D, Jess K, Weck R, Atzrodt J, Bannenberg T, Derdau V, Tamm M. Chem. Eur. J. 2019; 25: 6517
10e Becker D, Bockfeld D, Tamm M. Adv. Synth. Catal. 2022; 365: 367
10f Burhop A, Weck R, Atzrodt J, Derdau V. Eur. J. Org. Chem. 2017; 1418
10g Burhop A, Prohaska R, Weck R, Atzrodt J, Derdau V. J. Labelled Compd. Radiopharm. 2017; 60: 343
10h Valero M, Mishra A, Blass J, Weck R, Derdau V. ChemistryOpen 2019; 8: 1183
10i Kerr WJ, Knox GJ, Reid M, Tuttle T, Bergare J, Bragg RA. ACS Catal. 2020; 10: 11120

11a Garnett JL, Hodges RJ. Chem. Commun. 1967; 1220
11b Garnett JL, Hodges RJ. J. Am. Chem. Soc. 1967; 89: 4546
11c Hodges RJ, Garnett JL. J. Phys. Chem. 1968; 72: 1673
11d Hodges RJ, Garnett JL. J. Phys. Chem. 1969; 73: 1525
11e Garnett JL, Kenyon RS. J. Chem. Soc. D 1970; 698
11f Garnett JL, Kenyon RS. J. Chem. Soc. D 1971; 1227
11g Garnett JL, Long MA, McLaren AB, Peterson KB. J. Chem. Soc., Chem. Commun. 1973; 749
11h Blake MR, Garnett JL, Gregor IK, Hannan W, Hoa K, Long MA. J. Chem. Soc., Chem. Commun. 1975; 930
11i Gröll B, Schnürch M, Mihovilovic MD. J. Org. Chem. 2012; 77: 4432
11j Chen S, Song G, Li X. Tetrahedron Lett. 2008; 49: 6929
11k Eisele P, Ullwer F, Scholz S, Plietker B. Chem. Eur. J. 2019; 25: 16550
11l Eguillor B, Esteruelas MA, García-Raboso J, Oliván M, Oñate E. Organometallics 2009; 28: 3700
11m Alexakis E, Hickey MJ, Jones JR, Kingston LP, Lockley WJ. S, Mather AN, Smith T, Wilkinson DJ. Tetrahedron Lett. 2005; 46: 4291
11n Chaudret B. J. Organomet. Chem. 1984; 268: c33
11o Kratish Y, Bravo-Zhivotovskii D, Apeloig Y. ACS Omega 2017; 2: 372
11p Colebatch AL, Weller AS. Chem. Eur. J. 2018; 24: 5450
11q Connor BA, Rittle J, VanderVelde D, Peters JC. Organometallics 2016; 35: 686
11r Fryzuk MD, Rosenberg L, Rettig SJ. Organometallics 1991; 10: 2537
11s Ayed T, Barthelat J.-C, Tangour B, Pradère C, Donnadieu B, Grellier M, Sabo-Etienne S. Organometallics 2005; 24: 3824
11t Smart KA, Mothes Martin E, Annaka T, Grellier M, Sabo Etienne S. Adv. Synth. Catal. 2014; 356: 759

12a Hickman AJ, Villalobos JM, Sanford MS. Organometallics 2009; 28: 5316
12b Villalobos JM, Hickman AJ, Sanford MS. Organometallics 2010; 29: 257
12c Emmert MH, Gary JB, Villalobos JM, Sanford MS. Angew. Chem. Int. Ed. 2010; 49: 5884
12d Gary JB, Carter TJ, Sanford MS. Top. Catal. 2012; 55: 565
12e Hickman AJ, Cismesia MA, Sanford MS. Organometallics 2012; 31: 1761
12f Palmer WN, Chirik PJ. ACS Catal. 2017; 7: 5674
12g Yang H, Zarate C, Palmer WN, Rivera N, Hesk D, Chirik PJ. ACS Catal. 2018; 8: 10210
12h Zarate C, Yang H, Bezdek MJ, Hesk D, Chirik PJ. J. Am. Chem. Soc. 2019; 141: 5034
12i Giunta D, Hölscher M, Lehmann CW, Mynott R, Wirtz C, Leitner W. Adv. Synth. Catal. 2003; 345: 1139
12j Chen Q, Liu Q, Xiao J, Leng X, Deng L. J. Am. Chem. Soc. 2021; 143: 19956
12k Nelson DJ, Egbert JD, Nolan SP. Dalton Trans. 2013; 42: 4105
12l Fortman GC, Jacobsen H, Cavallo L, Nolan SP. Chem. Commun. 2011; 47: 9723

13a Iluc VM, Fedorov A, Grubbs RH. Organometallics 2012; 31: 39
13b Polukeev AV, Marcos R, Ahlquist MS. G, Wendt OF. Organometallics 2016; 35: 2600
13c Prechtl MH. G, Hölscher M, Ben-David Y, Theyssen N, Loschen R, Milstein D, Leitner W. Angew. Chem. Int. Ed. 2007; 46: 2269
13d Prechtl MH. G, Hölscher M, Ben-David Y, Theyssen N, Milstein D, Leitner W. Eur. J. Inorg. Chem. 2008; 3493
13e Ng SM, Lam WH, Mak CC, Tsang CW, Jia G, Lin Z, Lau CP. Organometallics 2003; 22: 641
13f Leung CW, Zheng W, Wang D, Ng SM, Yeung CH, Zhou Z, Lin Z, Lau CP. Organometallics 2007; 26: 1924
13g Rhinehart JL, Manbeck KA, Buzak SK, Lippa GM, Brennessel WW, Goldberg KI, Jones WD. Organometallics 2012; 31: 1943
13h Esteruelas MA, Martínez A, Oliván M, Vélez A. J. Org. Chem. 2020; 85: 15693
13i Kramer M, Watts D, Vedernikov AN. Organometallics 2020; 39: 4102

14a Pony Yu R, Hesk D, Rivera N, Pelczer I, Chirik PJ. Nature 2016; 529: 195
14b Corpas J, Viereck P, Chirik PJ. ACS Catal. 2020; 10: 8640
14c Garhwal S, Kaushansky A, Fridman N, Shimon LJ. W, de Ruiter G. J. Am. Chem. Soc. 2020; 142: 17131
14d Cummins AW. M, Li S, Willcox DR, Muilu T, Docherty JH, Thomas SP. Tetrahedron 2020; 76: 131084
14e Roque JB, Pabst TP, Chirik PJ. ACS Catal. 2022; 12: 8877

15a Golden JT, Andersen RA, Bergman RG. J. Am. Chem. Soc. 2001; 123: 5837
15b Yung CM, Skaddan MB, Bergman RG. J. Am. Chem. Soc. 2004; 126: 13033
15c Klei SR, Golden JT, Tilley TD, Bergman RG. J. Am. Chem. Soc. 2002; 124: 2092
15d Skaddan MB, Yung CM, Bergman RG. Org. Lett. 2004; 6: 11
15e Skaddan MB, Bergman RG. J. Labelled Compd. Radiopharm. 2006; 49: 623
15f Corberán R, Sanaú M, Peris E. J. Am. Chem. Soc. 2006; 128: 3974
15g Feng Y, Jiang B, Boyle PA, Ison EA. Organometallics 2010; 29: 2857
15h Lehman MC, Gary JB, Boyle PD, Sanford MS, Ison EA. ACS Catal. 2013; 3: 2304
15i Mai VH, Gadzhiev OB, Ignatov SK, Nikonov GI. Catal. Sci. Technol. 2019; 9: 3398
15j Piola L, Fernández-Salas JA, Manzini S, Nolan SP. Org. Biomol. Chem. 2014; 12: 8683
15k Prades A, Poyatos M, Peris E. Adv. Synth. Catal. 2010; 352: 1155
15l Zhao L.-L, Liu W, Zhang Z, Zhao H, Wang Q, Yan X. Org. Lett. 2019; 21: 10023
15m Campos J, Esqueda AC, López-Serrano J, Sánchez L, Cossio FP, De Cozar A, Álvarez E, Maya C, Carmona E. J. Am. Chem. Soc. 2010; 132: 16765

16a Gorelsky SI, Lapointe D, Fagnou K. J. Am. Chem. Soc. 2008; 130: 10848
16b Ackermann L. Chem. Rev. 2011; 111: 1315
16c Wu K, Lam N, Strassfeld DA, Fan Z, Qiao JX, Liu T, Stamos D, Yu JQ. Angew. Chem. Int. Ed. 2024; 63: e202400509
16d Ma S, Villa G, Thuy-Boun PS, Homs A, Yu J.-Q. Angew. Chem. Int. Ed. 2014; 53: 734
16e Müller V, Weck R, Derdau V, Ackermann L. ChemCatChem 2020; 12: 100
16f Garreau AL, Zhou H, Young MC. Org. Lett. 2019; 21: 7044
16g Zhang Z, Jiang Z.-J, Cao Y, Chen J, Gao Z. Synthesis 2022; 54: 4907
16h Hirano M, Fujimoto R, Hatagami K, Komine N, Komiya S. ChemCatChem 2013; 5: 1101

17a Giles R, Ahn G, Jung KW. Tetrahedron Lett. 2015; 56: 6231
17b Uttry A, Mal S, van Gemmeren M. J. Am. Chem. Soc. 2021; 143: 10895
17c Zheng C, Xue J, Jiang ZJ, Han J, Wang J, Bai JF, Chen J, Gao Z. Chem. Commun. 2024; 60: 10338
17d Liu W, Xu X, Zhao H, Yan X. Tetrahedron 2018; 74: 4111
17e Zhao D, Luo H, Chen B, Chen W, Zhang G, Yu Y. J. Org. Chem. 2018; 83: 7860
17f Sheng F.-F, Gu J.-G, Liu K.-H, Zhang H.-H. J. Org. Chem. 2022; 87: 16084
17g Yin D.-W, Liu G. J. Org. Chem. 2018; 83: 3987

18a Fitzgerald LS, McNulty RL, Greener A, O’Duill ML. J. Org. Chem. 2023; 88: 10772
18b Wu J, Qian B, Lu L, Yang H, Shang Y, Zhang J. Org. Chem. Front. 2021; 8: 3032
18c Peng W, Liu Q, Yin F, Shi C, Ji L, Qu L, Wang C, Luo H, Kong L, Wang X. RSC Adv. 2021; 11: 8356
18d Zhang J, Zhang S, Gogula T, Zou H. ACS Catal. 2020; 10: 7486
18e Ko SL, Courtney E, Light DM, Jones DD, McGlacken DG. P. Tetrahedron Green Chem 2023; 2: 100019
18f Jiang Z.-J, Xu S.-H, Su Y, Hu E, Han J, Bai J.-F, Tang B, Chen J, Gao Z. Chem. Commun. 2024; 60: 384
18g Young KJ. H, Lokare KS, Leung CH, Cheng M.-J, Nielsen RJ, Petasis NA, Goddard WA, Periana RA. J. Mol. Catal. A: Chem. 2011; 339: 17
18h Su Y, Jiang Z.-J, Han J, Duan L, Bai J.-F, Chen J, Gao Z. Chem. Eur. J. 2024; in press; DOI

19a Li E.-C, Hu G.-Q, Zhu Y.-X, Zhang H.-H, Shen K, Hang X.-C, Zhang C, Huang W. Org. Lett. 2019; 21: 6745
19b Tlahuext-Aca A, Hartwig JF. ACS Catal. 2021; 11: 1119
19c Sheng F.-F, Li E.-C, Bai J.-W, Wang C.-X, Hu G.-Q, Liu K.-H, Sun Z.-Y, Shen K, Zhang H.-H. Org. Biomol. Chem. 2022; 20: 1176
19d Hu G.-Q, Li E.-C, Zhang H.-H, Huang W. Org. Biomol. Chem. 2020; 18: 6627
19e Hu G.-Q, Bai J.-W, Li E.-C, Liu K.-H, Sheng F.-F, Zhang H.-H. Org. Lett. 2021; 23: 1554
19f Tang J, Kong J, Xu H, Jiang Z.-J, She Y, Bai J, Tang B, Chen J, Gao Z, Gao K. J. Org. Chem. 2023; 88: 1560
19g Xu H, Jiang ZJ, Jia Y, Su Y, Bai JF, Gao Z, Chen J, Gao K. J. Org. Chem. 2024; 89: 8468

20a Leow D, Li G, Mei TS, Yu JQ. Nature 2012; 486: 518
20b Tang RY, Li G, Yu JQ. Nature 2014; 507: 215
20c Dey A, Sinha SK, Achar TK, Maiti D. Angew. Chem. Int. Ed. 2019; 58: 10820
20d Dutta U, Maiti D. Acc. Chem. Res. 2022; 55: 354
20e Bag S, Petzold M, Sur A, Bhowmick S, Werz DB, Maiti D. Chem. Eur. J. 2019; 25: 9433
20f Xu H, Liu M, Li L.-J, Cao Y.-F, Yu J.-Q, Dai H.-X. Org. Lett. 2019; 21: 4887

21a Kopf S, Neumann H, Beller M. Chem. Commun. 2021; 57: 1137
21b Kong J, Jiang Z.-J, Xu J, Li Y, Cao H, Ding Y, Tang B, Chen J, Gao Z. J. Org. Chem. 2021; 86: 13350
21c Zheng C, Jiang Z.-J, Jin K, Wang Q, Bai J.-F, Xu G, Gao Z. J. Org. Chem. 2023; 88: 17164
21d Kopf S, Ye F, Neumann H, Beller M. Chem. Eur. J. 2021; 27: 9768

22a Farizyan M, Mondal A, Mal S, Deufel F, van Gemmeren M. J. Am. Chem. Soc. 2021; 143: 16370
22b Dey J, Kaltenberger S, van Gemmeren M. Angew. Chem. Int. Ed. 2024; 63: e202404421
22c Dey J, van Gemmeren M. Synlett 2024; 35: 2191
22d Yun SJ, Kim J, Kang E, Jung H, Kim HT, Kim M, Joo JM. ACS Catal. 2023; 13: 4042
22e Werz DB, Teja C, Kolb S, Colonna P, Grover J, Lahiri GK, Pieters G, Maiti D, Garcia-Argote S. Angew. Chem. Int. Ed. 2024; 63: e202410162

23a Reed-Berendt BG, Latham DE, Dambatta MB, Morrill LC. ACS. Cent. Sci. 2021; 7: 570
23b Corma A, Navas J, Sabater MJ. Chem. Rev. 2018; 118: 1410
23c Michelotti A, Roche M. Synthesis 2019; 51: 1319
23d Takahashi M, Oshima K, Matsubara S. Chem. Lett. 2005; 34: 192
23e Bossi G, Putignano E, Rigo P, Baratta W. Dalton Trans. 2011; 40: 8986
23f Itoga M, Yamanishi M, Udagawa T, Kobayashi A, Maekawa K, Takemoto Y, Naka H. Chem. Sci. 2022; 13: 8744
23g Chatterjee B, Gunanathan C. Org. Lett. 2015; 17: 4794
23h Zhang L, Nguyen DH, Raffa G, Desset S, Paul S, Dumeignil F, Gauvin RM. Catal. Commun. 2016; 84: 67
23i Kar S, Goeppert A, Sen R, Kothandaraman J, Prakash GK. S. Green Chem. 2018; 20: 2706
23j Khaskin E, Milstein D. ACS Catal. 2013; 3: 448
23k Tse SK. S, Xue P, Lau CW. S, Sung HH. Y, Williams ID, Jia G. Chem. Eur. J. 2011; 17: 13918
23l Bai W, Lee K.-H, Tse SK. S, Chan KW, Lin Z, Jia G. Organometallics 2015; 34: 3686

24a Neubert L, Michalik D, Bähn S, Imm S, Neumann H, Atzrodt J, Derdau V, Holla W, Beller M. J. Am. Chem. Soc. 2012; 134: 12239
24b Chatterjee B, Krishnakumar V, Gunanathan C. Org. Lett. 2016; 18: 5892
24c Hale LV. A, Szymczak NK. J. Am. Chem. Soc. 2016; 138: 13489
24d Krishnakumar V, Gunanathan C. Chem. Commun. 2018; 54: 8705
24e Guo B, Vries JG, Otten E. Adv. Synth. Catal. 2022; 364: 179
24f Chatterjee B, Gunanathan C. Chem. Commun. 2016; 52: 4509

25a Faller JW, Smart CJ. Organometallics 1989; 8: 602
25b Kohl G, Rudolph R, Pritzkow H, Enders M. Organometallics 2005; 24: 4774
25c Di Giuseppe A, Castarlenas R, Pérez-Torrente JJ, Lahoz FJ, Oro LA. Chem. Eur. J. 2014; 20: 8391
25d Lenges CP, White PS, Brookhart M. J. Am. Chem. Soc. 1999; 121: 4385
25e Lenges CP, White PS, Marshall WJ, Brookhart M. Organometallics 2000; 19: 1247
25f Lenges CP, Brookhart M. J. Am. Chem. Soc. 1997; 119: 3165
25g Lenges CP, Brookhart M, Grant BE. J. Organomet. Chem. 1997; 528: 199
25h Lenges CP, White PS, Brookhart M. J. Am. Chem. Soc. 1998; 120: 6965
25i Tse SK. S, Xue P, Lin Z, Jia G. Adv. Synth. Catal. 2010; 352: 1512
25j Camedda N, Serafino A, Maggi R, Bigi F, Cera G, Maestri G. Synthesis 2020; 52: 1762
25k Hatano M, Nishimura T, Yorimitsu H. Org. Lett. 2016; 18: 3674
25l Bechtoldt A, Ackermann L. ChemCatChem 2019; 11: 435
25m Di Giuseppe A, Castarlenas R, Pérez-Torrente JJ, Lahoz FJ, Polo V, Oro LA. Angew. Chem. Int. Ed. 2011; 50: 3938
25n Erdogan G, Grotjahn DB. J. Am. Chem. Soc. 2009; 131: 10354
25o Erdogan G, Grotjahn DB. Top. Catal. 2010; 53: 1055
25p Smarun AV, Petković M, Shchepinov MS, Vidović D. J. Org. Chem. 2017; 82: 13115
25q Cramer R. J. Am. Chem. Soc. 1966; 88: 2272
25r Ishibashi K, Takahashi M, Yokota Y, Oshima K, Matsubara S. Chem. Lett. 2005; 34: 664
25s Cera G, Della Ca’ N, Maestri G. Chem. Sci. 2019; 10: 10297

26a Dong B, Cong X, Hao N. RSC Adv. 2020; 10: 25475
26b Bourriquen F, Junge K, Beller M. Synlett 2023; 34: 332
26c Bai J.-W, Guo L, Chen M.-Z, Advincula R, Zhang H.-H. Tetrahedron Lett. 2024; 135: 154884

27a Kang QK, Li Y, Chen K, Zhu H, Wu WQ, Lin Y, Shi H. Angew. Chem. Int. Ed. 2022; 61: e202117381
27b Lu J.-L, Deng J.-T, Lang M, Peng J.-B. Org. Chem. Front. 2024; 11: 5473

28 Linford-Wood TG, Mahon MF, Grayson MN, Webster RL. ACS Catal. 2022; 12: 2979
29 Wu D.-C, Bai J.-W, Guo L, Hu G.-Q, Liu K.-H, Sheng F.-F, Zhang H.-H, Sun Z.-Y, Shen K, Liu X. Tetrahedron Lett. 2021; 66: 152807

30a Guo Q.-X, Shen B.-J, Guo H.-Q, Takahashi T. Chin. J. Chem. 2005; 23: 341
30b Garnett JL, Long MA, Vining RF. W, Mole T. J. Am. Chem. Soc. 1972; 94: 5913
30c Long MA, Garnett JL, Vining RF. W, Mole T. J. Am. Chem. Soc. 1972; 94: 8632
30d Long MA, Garnett JL, Vining RF. W. J. Chem. Soc., Perkin Trans. 2 1975; 1298

31a Brown WG, Garnett JL. J. Am. Chem. Soc. 1958; 80: 5272
31b Norton R. J. Catal. 1975; 39: 53
31c Maeda M, Ogawa O, Kawazoe Y. Chem. Pharm. Bull. 1977; 25: 3329
31d Yamamoto M, Yokota Y, Oshima K, Matsubara S. Chem. Commun. 2004; 1714
31e Barthez JM, Filikov AV, Frederiksen LB, Huguet M.-L, Jones JR, Lu S.-Y. Can. J. Chem. 1998; 76: 726

32a Sajiki H, Hattori K, Aoki F, Yasunaga K, Hirota K. Synlett 2002; 1149
32b Sajiki H, Aoki F, Esaki H, Maegawa T, Hirota K. Org. Lett. 2004; 6: 1485
32c Esaki H, Aoki F, Umemura M, Kato M, Maegawa T, Monguchi Y, Sajiki H. Chem. Eur. J. 2007; 13: 4052
32d Kurita T, Hattori K, Seki S, Mizumoto T, Aoki F, Yamada Y, Ikawa K, Maegawa T, Monguchi Y, Sajiki H. Chem. Eur. J. 2008; 14: 664
32e Sajiki H, Kurita T, Esaki H, Aoki F, Maegawa T, Hirota K. Org. Lett. 2004; 6: 3521
32f Kurita T, Aoki F, Mizumoto T, Maejima T, Esaki H, Maegawa T, Monguchi Y, Sajiki H. Chem. Eur. J. 2008; 14: 3371
32g Sajiki H, Ito N, Esaki H, Maesawa T, Maegawa T, Hirota K. Tetrahedron Lett. 2005; 46: 6995
32h Derdau V, Atzrodt J, Zimmermann J, Kroll C, Brückner F. Chem. Eur. J. 2009; 15: 10397
32i Shen H, Liu Y, Tian X, Zhang X, Zhang Y. ChemistrySelect 2018; 3: 8724
32j Sajiki H, Esaki H, Aoki F, Maegawa T, Hirota K. Synlett 2005; 1385
32k Sajiki H, Esaki H, Aoki F, Maegawa T, Hirota K. Heterocycles 2005; 66: 361
32l Esaki H, Ohtaki R, Maegawa T, Monguchi Y, Sajiki H. J. Org. Chem. 2007; 72: 2143
32m Maegawa T, Akashi A, Esaki H, Aoki F, Sajiki H, Hirota K. Synlett 2005; 845
32n Esaki H, Ito N, Sakai S, Maegawa T, Monguchi Y, Sajiki H. Tetrahedron 2006; 62: 10954
32o Atzrodt J, Derdau V. J. Labelled Compd. Radiopharm. 2010; 53: 674

33a Ito N, Esaki H, Maesawa T, Imamiya E, Maegawa T, Sajiki H. Bull. Chem. Soc. Jpn. 2008; 81: 278
33b Ito N, Watahiki T, Maesawa T, Maegawa T, Sajiki H. Adv. Synth. Catal. 2006; 348: 1025
33c Ito N, Watahiki T, Maesawa T, Maegawa T, Sajiki H. Synthesis 2008; 1467
33d Maegawa T, Ito N, Oono K, Monguchi Y, Sajiki H. Synthesis 2009; 2674

34a Maegawa T, Fujiwara Y, Inagaki Y, Esaki H, Monguchi Y, Sajiki H. Angew. Chem. Int. Ed. 2008; 47: 5394
34b Fujiwara Y, Iwata H, Sawama Y, Monguchi Y, Sajiki H. Chem. Commun. 2010; 46: 4977
34c Cioffi EA. Tetrahedron Lett. 1996; 37: 6231
34d Cioffi EA, Willis WS, Suib SL. Langmuir 1990; 6: 404
34e Cioffi EA, Willis WS, Suib SL. Langmuir 1988; 4: 697

35a Gao L, Perato S, Garcia-Argote S, Taglang C, Martínez-Prieto LM, Chollet C, Buisson D.-A, Dauvois V, Lesot P, Chaudret B, Rousseau B, Feuillastre S, Pieters G. Chem. Commun. 2018; 54: 2986
35b Maegawa T, Fujiwara Y, Inagaki Y, Monguchi Y, Sajiki H. Adv. Synth. Catal. 2008; 350: 2215
35c Sawama Y, Yabe Y, Iwata H, Fujiwara Y, Monguchi Y, Sajiki H. Chem. Eur. J. 2012; 18: 16436

36a Sawama Y, Yamada T, Yabe Y, Morita K, Shibata K, Shigetsura M, Monguchi Y, Sajiki H. Adv. Synth. Catal. 2013; 355: 1529
36b Yamada T, Sawama Y, Shibata K, Morita K, Monguchi Y, Sajiki H. RSC Adv. 2015; 5: 13727
36c Yamada T, Park K, Yasukawa N, Morita K, Monguchi Y, Sawama Y, Sajiki H. Adv. Synth. Catal. 2016; 358: 3277
36d Park K, Matsuda T, Yamada T, Monguchi Y, Sawama Y, Doi N, Sasai Y, Kondo S. i, Sawama Y, Sajiki H. Adv. Synth. Catal. 2018; 360: 2303
36e Sawama Y, Nakano A, Matsuda T, Kawajiri T, Yamada T, Sajiki H. Org. Process Res. Dev. 2019; 23: 648
36f Sawama Y, Matsuda T, Moriyama S, Ban K, Fujioka H, Kamiya M, Shou J, Ozeki Y, Akai S, Sajiki H. Asian J. Org. Chem. 2023; 12: e202200710
36g Moriyama S, Mae M, Shibata D, Yamakoshi H, Kajimoto S, Nakabayashi T, Ishimoto T, Mogi K, Sajiki H, Akai S, Sawama Y. Chem. Commun. 2023; 59: 12100

37 Park K, Oka N, Sawama Y, Ikawa T, Yamada T, Sajiki H. Org. Chem. Front. 2022; 9: 1986

38a Philippot K, Chaudret B. C. R. Chim. 2003; 6: 1019
38b Pery T, Pelzer K, Buntkowsky G, Philippot K, Limbach HH, Chaudret B. ChemPhysChem 2005; 6: 605
38c García-Antón J, Axet MR, Jansat S, Philippot K, Chaudret B, Pery T, Buntkowsky G, Limbach HH. Angew. Chem. Int. Ed. 2008; 47: 2074
38d Pieters G, Taglang C, Bonnefille E, Gutmann T, Puente C, Berthet JC, Dugave C, Chaudret B, Rousseau B. Angew. Chem. Int. Ed. 2014; 53: 230
38e Pfeifer V, Certiat M, Bouzouita D, Palazzolo A, Garcia-Argote S, Marcon E, Buisson DA, Lesot P, Maron L, Chaudret B, Tricard S, Rosal I, Poteau R, Feuillastre S, Pieters G. Chem. Eur. J. 2020; 26: 4988
38f Taglang C, Martínez-Prieto LM, del Rosal I, Maron L, Poteau R, Philippot K, Chaudret B, Perato S, Sam Lone A, Puente C, Dugave C, Rousseau B, Pieters G. Angew. Chem. Int. Ed. 2015; 54: 10474
38g Bresó-Femenia E, Godard C, Claver C, Chaudret B, Castillón S. Chem. Commun. 2015; 51: 16342
38h Palazzolo A, Feuillastre S, Pfeifer V, Garcia-Argote S, Bouzouita D, Tricard S, Chollet C, Marcon E, Buisson DA, Cholet S, Fenaille F, Lippens G, Chaudret B, Pieters G. Angew. Chem. Int. Ed. 2019; 58: 4891
38i Pfeifer V, Zeltner T, Fackler C, Kraemer A, Thoma J, Zeller A, Kiesling R. Angew. Chem. Int. Ed. 2021; 60: 26671
38j Guy KA, Shapley JR. Organometallics 2009; 28: 4020

39a Martínez-Prieto LM, Baquero EA, Pieters G, Flores JC, De Jesús E, Nayral C, Delpech F, van Leeuwen PW. N. M, Lippens G, Chaudret B. Chem. Commun. 2017; 53: 5850
39b Suárez-Riaño O, Mencia G, Tricard S, Esvan J, Fazzini P.-F, Chaudret B, Baquero EA. Chem. Commun. 2023; 59: 1062
39c Zuluaga-Villamil A, Mencia G, Asensio JM, Fazzini P.-F, Baquero EA, Chaudret B. Organometallics 2022; 41: 3313
39d Martinez-Espinar F, Salom-Català A, Bresó-Femenia E, Claver C, Baletto F, Ricart JM, Chaudret B, Carbó JJ, Godard C, Castillon S. Inorg. Chem. 2023; 62: 4570
39e Palazzolo A, Naret T, Daniel-Bertrand M, Buisson DA, Tricard S, Lesot P, Coppel Y, Chaudret B, Feuillastre S, Pieters G. Angew. Chem. Int. Ed. 2020; 59: 20879
39f Bouzouita D, Asensio JM, Pfeifer V, Palazzolo A, Lecante P, Pieters G, Feuillastre S, Tricard S, Chaudret B. Nanoscale 2020; 12: 15736
39g Valero M, Bouzouita D, Palazzolo A, Atzrodt J, Dugave C, Tricard S, Feuillastre S, Pieters G, Chaudret B, Derdau V. Angew. Chem. Int. Ed. 2020; 59: 3517
39h Molinillo P, Puyo M, Vattier F, Lacroix B, Rendón N, Lara P, Suárez A. Nanoscale 2023; 15: 14488
39i Levernier E, Tatoueix K, Garcia-Argote S, Pfeifer V, Kiesling R, Gravel E, Feuillastre S, Pieters G. JACS Au 2022; 2: 801

40a Li W, Rabeah J, Bourriquen F, Yang D, Kreyenschulte C, Rockstroh N, Lund H, Bartling S, Surkus A.-E, Junge K, Brückner A, Lei A, Beller M. Nat. Chem. 2022; 14: 334
40b Bourriquen F, Rockstroh N, Bartling S, Junge K, Beller M. Angew. Chem. Int. Ed. 2022; 61: e202202423
40c Shao F, Wang K, Jiang W, Xu Z, Li X, Zhong X, Wang J. ACS Catal. 2023; 13: 15746
40d Mencia G, Rouan P, Fazzini P.-F, Kulyk H, Varela-Izquierdo V, Lippens G, Chaudret B. Catal. Sci. Technol. 2024; 14: 4904
40e Shao F, Ma F, Li Y, Jiang W, Wei Z, Zhong X, Wang H, Wang L, Wang J. ChemSusChem 2023; 16: e202202395
40f Jiang W, Shao F, Cheng J, Ma F, Wei Z, Zhong X, Wang H, Wang J. Asian J. Org. Chem. 2023; 12: e202200662