Transition Metal-Catalyzed Directed C(sp3)–H Functionalization of Saturated Heterocycles

Daniele Antermite; James A. Bull

doi:10.1055/s-0037-1611822

Synthesis, Inhaltsverzeichnis

Synthesis 2019; 51(17): 3171-3204
DOI: 10.1055/s-0037-1611822

review

Transition Metal-Catalyzed Directed C(sp³)–H Functionalization of Saturated Heterocycles

Daniele Antermite

,

James A. Bull ∗

Abstract

Alle Artikel dieser Rubrik

Abstract

Synthetic methods that can readily access saturated heterocycles with different substitution patterns and with control of stereo- and regiochemistry are of huge potential value in the development of new medicinal compounds. Directed C–H functionalization of simple and commercially available precursors offers the potential to prepare diverse collections of such valuable compounds that can probe the different available exit vectors from a ring system. Nonetheless, the presence of the Lewis basic heteroatoms makes this a significant challenge. This review covers recent advances in the catalytic C–H functionalization of saturated heterocycles, with a view to different heterocycles (N, O, S), substitution patterns and transformations.

1 Introduction

2 α-C–H Functionalization with Directing Group on Nitrogen

3 C–H Functionalization at Unactivated C(3), C(4), and C(5) Positions

3.1 C–H Functionalization at C(3) with Directing Groups at C(2)

3.2 C–H Functionalization at C(3), C(4), and C(5): Directing Groups at C(4) and C(3)

4 Transannular C–H Functionalization

5 Conclusion

Key words

C–H functionalization - saturated heterocycles - transition metal catalysis - stereoselectivity - regioselectivity

Volltext

Referenzen

References

1a Taylor RD, MacCoss M, Lawson AD. G. J. Med. Chem. 2014; 57: 5845
1b Aldeghi M, Malhotra S, Selwood DL, Chan AW. E. Chem. Biol. Drug Des. 2014; 83: 450
1c Vitaku E, Smith DT, Njardarson JT. J. Med. Chem. 2014; 57: 10257

2a O’Hagan D. Nat. Prod. Rep. 2000; 17: 435
2b Saleem M, Kim HJ, Ali MS, Lee YS. Nat. Prod. Rep. 2005; 22: 696
2c Galliford CV, Scheidt KA. Angew. Chem. Int. Ed. 2007; 46: 8748
2d Lorente A, Lamariano-Merketegi J, Albericio F, Álvarez M. Chem. Rev. 2013; 113: 4567

3 Blakemore DC, Castro L, Churcher I, Rees DC, Thomas AW, Wilson DM, Wood A. Nat. Chem. 2018; 10: 383

4a Lovering F, Bikker J, Humblet C. J. Med. Chem. 2009; 52: 6752
4b Lovering F. Med. Chem. Commun. 2013; 4: 515
4c Nadin A, Hattotuwagama C, Churcher I. Angew. Chem. Int. Ed. 2012; 51: 1114
4d Murray CW, Rees DC. Angew. Chem. Int. Ed. 2016; 55: 488

5a Godula K, Sames D. Science 2006; 312: 67
5b Wencel-Delord J, Dröge T, Liu F, Glorius F. Chem. Soc. Rev. 2011; 40: 4740
5c McMurray L, O’Hara F, Gaunt MJ. Chem. Soc. Rev. 2011; 40: 1885
5d Yamaguchi J, Yamaguchi AD, Itami K. Angew. Chem. Int. Ed. 2012; 51: 8960
5e Wencel-Delord J, Glorius F. Nat. Chem. 2013; 5: 369
5f Wang W, Lorion MM, Shah J, Kapdi AR, Ackermann L. Angew. Chem. Int. Ed. 2018; 57: 14700

6a Boutadla Y, Davies DL, Macgregor SA, Poblador-Bahamonde AI. Dalton Trans. 2009; 5820
6b Lapointe D, Fagnou K. Chem. Lett. 2010; 39: 1118
6c Ackermann L. Chem. Rev. 2011; 111: 1315
6d Davies DL, Macgregor SA, McMullin CL. Chem. Rev. 2017; 117: 8649

For recent selected examples of late-stage C–H functionalization see:

7a Larsen MA, Hartwig JF. J. Am. Chem. Soc. 2014; 136: 4287
7b Wang W, Lorion MM, Martinazzoli O, Ackermann L. Angew. Chem. Int. Ed. 2018; 57: 10554
7c Simonetti M, Cannas DM, Just-Baringo X, Vitorica-Yrezabal IJ, Larrosa I. Nat. Chem. 2018; 10: 724

8a Alberico D, Scott ME, Lautens M. Chem. Rev. 2007; 107: 174
8b Ackermann L, Vicente R, Kapdi AR. Angew. Chem. Int. Ed. 2009; 48: 9792
8c Ping L, Chung DS, Bouffard J, Lee S. Chem. Soc. Rev. 2017; 46: 4299
8d Mihai MT, Genov GR, Phipps RJ. Chem. Soc. Rev. 2018; 47: 149

9a Baudoin O. Chem. Soc. Rev. 2011; 40: 4902
9b Dastbaravardeh N, Christakakou M, Haider M, Schnürch M. Synthesis 2014; 46: 1421
9c Bruneau C. In Ruthenium in Catalysis . Dixneuf PH, Bruneau C. Springer; Cham: 2014: 195
9d He J, Wasa M, Chan KS. L, Shao Q, Yu J.-Q. Chem. Rev. 2017; 117: 8754
9e Chu JC. K, Rovis T. Angew. Chem. Int. Ed. 2018; 57: 62

10a Rouquet G, Chatani N. Angew. Chem. Int. Ed. 2013; 52: 11726
10b Zhang M, Zhang Y, Jie X, Zhao H, Li G, Su W. Org. Chem. Front. 2014; 1: 843
10c Chen Z, Wang B, Zhang J, Yu W, Liu Z, Zhang Y. Org. Chem. Front. 2015; 2: 1107
10d Daugulis O, Roane J, Tran LD. Acc. Chem. Res. 2015; 48: 1053
10e Xu Y, Dong G. Chem. Sci. 2018; 9: 1424
10f Sambiagio C, Schönbauer D, Blieck R, Dao-Huy T, Pototschnig G, Schaaf P, Wiesinger T, Zia MF, Wencel-Delord J, Besset T, Maes BU. W, Schnürch M. Chem. Soc. Rev. 2018; 47: 6603

11a Zaitsev VG, Shabashov D, Daugulis O. J. Am. Chem. Soc. 2005; 127: 13154
11b Shabashov D, Daugulis O. J. Am. Chem. Soc. 2010; 132: 3965

12a Giri R, Maugel N, Li J.-J, Wang D.-H, Breazzano SP, Saunders LB, Yu J.-Q. J. Am. Chem. Soc. 2007; 129: 3510
12b Shi B.-F, Maugel N, Zhang Y.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2008; 47: 4882

For selected examples see:

13a Feng Y, Chen G. Angew. Chem. Int. Ed. 2010; 49: 958
13b Gutekunst WR, Gianatassio R, Baran PS. Angew. Chem. Int. Ed. 2012; 51: 7507
13c Roman DS, Charette AB. Org. Lett. 2013; 15: 4394
13d Yan S.-B, Zhang S, Duan W.-L. Org. Lett. 2015; 17: 2458
13e Chapman LM, Beck JC, Wu L, Reisman SE. J. Am. Chem. Soc. 2016; 138: 9803
13f Zhang X, Lu G, Sun M, Mahankali M, Ma Y, Zhang M, Hua W, Hu Y, Wang Q, Chen J, He G, Qi X, Shen W, Liu P, Chen G. Nat. Chem. 2018; 10: 540

For reviews see:

14a Engle KM, Mei T.-S, Wasa M, Yu J.-Q. Acc. Chem. Res. 2012; 45: 788
14b Yang Y.-F, Hong X, Yu J.-Q, Houk KN. Acc. Chem. Res. 2017; 50: 2853

For selected recent examples see:

14c Chu L, Xiao K.-J, Yu J.-Q. Science 2014; 346: 451
14d Chan KS. L, Fu H.-Y, Yu J.-Q. J. Am. Chem. Soc. 2015; 137: 2042
14e Chen G, Gong W, Zhuang Z, Andrä MS, Chen Y.-Q, Hong X, Yang Y.-F, Liu T, Houk KN, Yu J.-Q. Science 2016; 353: 1023
14f Wu Q.-F, Shen P.-X, He J, Wang X.-B, Zhang F, Shao Q, Zhu R.-Y, Mapelli C, Qiao JX, Poss MA, Yu J.-Q. Science 2017; 355: 499
14g He J, Shao Q, Wu Q, Yu J.-Q. J. Am. Chem. Soc. 2017; 139: 3344
14h Shen P.-X, Hu L, Shao Q, Hong K, Yu J.-Q. J. Am. Chem. Soc. 2018; 140: 6545

For selected examples see:

15a Chen F.-J, Zhao S, Hu F, Chen K, Zhang Q, Zhang S.-Q, Shi B.-F. Chem. Sci. 2013; 4: 4187
15b He G, Zhang S.-Y, Nack WA, Li Q, Chen G. Angew. Chem. Int. Ed. 2013; 52: 11124
15c Rodríguez N, Romero-Revilla JA, Fernández-Ibáñez M. Á, Carretero JC. Chem. Sci. 2013; 4: 175
15d Fan M, Ma D. Angew. Chem. Int. Ed. 2013; 52: 12152
15e Xu Y, Yan G, Ren Z, Dong G. Nat. Chem. 2015; 7: 829
15f Zhang Y.-F, Zhao H.-W, Wang H, Wei J.-B, Shi Z.-J. Angew. Chem. Int. Ed. 2015; 54: 13686
15g Knight BJ, Rothbaum JO, Ferreira EM. Chem. Sci. 2016; 7: 1982

For a recent review, see:

16a St John-Campbell S, Bull JA. Org. Biomol. Chem. 2018; 16: 4582

For selected examples see:

16b Zhang F.-L, Hong K, Li T.-J, Park H, Yu J.-Q. Science 2016; 351: 252
16c Yang K, Li Q, Liu Y, Li G, Ge H. J. Am. Chem. Soc. 2016; 138: 12775
16d Wu Y, Chen Y.-Q, Liu T, Eastgate MD, Yu J.-Q. J. Am. Chem. Soc. 2016; 138: 14554
16e St John-Campbell S, White AJ. P, Bull JA. Chem. Sci. 2017; 8: 4840
16f Liu Y, Ge H. Nat. Chem. 2017; 9: 26
16g St John-Campbell S, Ou AK, Bull JA. Chem. Eur. J. 2018; 24: 17838
16h Kapoor M, Liu D, Young MC. J. Am. Chem. Soc. 2018; 140: 6818

17a Davies HM. L, Manning JR. Nature 2008; 451: 417
17b Doyle MP, Duffy R, Ratnikov M, Zhou L. Chem. Rev. 2010; 110: 704

For recent selected examples, see:

17c He J, Hamann LG, Davies HL. M, Beckwith RE. J. Nat. Commun. 2015; 6: 5943
17d Bedell TA, Hone GA. B, Valette D, Yu J.-Q, Davies HM. L, Sorensen EJ. Angew. Chem. Int. Ed. 2016; 55: 8270

18a Rueping M, Vila C, Koenigs RM, Poscharny K, Fabry DC. Chem. Commun. 2011; 47: 2360
18b Hari DP, König B. Org. Lett. 2011; 13: 3852
18c Beatty JW, Stephenson CR. J. Acc. Chem. Res. 2015; 48: 1474

19a Li C.-J. Acc. Chem. Res. 2009; 42: 335
19b Klussmann M, Sureshkumar D. Synthesis 2011; 353
19c Girard SA, Knauber T, Li C.-J. Angew. Chem. Int. Ed. 2014; 53: 74

For hydrogen atom transfer strategies, see:

20a Yoshikai N, Mieczkowski A, Matsumoto A, Ilies L, Nakamura E. J. Am. Chem. Soc. 2010; 132: 5568
20b Capaldo L, Ravelli D. Eur. J. Org. Chem. 2017; 2017: 2056

21 For Ni-catalyzed C–H functionalization of tetrahydrofuran by radical abstraction, see: Liu D, Liu C, Li H, Lei A. Angew. Chem. Int. Ed. 2013; 52: 4453

For photoredox-mediated approaches, see:

22a McNally A, Prier CK, MacMillan DW. C. Science 2011; 334: 1114
22b Noble A, MacMillan DW. C. J. Am. Chem. Soc. 2014; 136: 11602
22c Prier CK, MacMillan DW. C. Chem. Sci. 2014; 5: 4173
22d Joe CL, Doyle AG. Angew. Chem. Int. Ed. 2016; 55: 4040
22e Ahneman DT, Doyle AG. Chem. Sci. 2016; 7: 7002
22f Shaw MH, Shurtleff VW, Terrett JA, Cuthbertson JD, MacMillan DW. C. Science 2016; 352: 1304
22g Perry IB, Brewer TF, Sarver PJ, Schultz DM, DiRocco DA, MacMillan DW. C. Nature 2018; 560: 70
22h Grainger R, Heightman TD, Ley SL, Lima F, Johnson CN. Chem. Sci. 2019; 10: 2264

23 For Fe-catalyzed C–H oxidation of pyrrolidine ring, see: Osberger TJ, Rogness DC, Kohrt JT, Stepan AF, White MC. Nature 2016; 537: 214

For selected examples proceeding by hydride transfer, see:

24a Jurberg ID, Peng B, Wöstefeld E, Wasserloos M, Maulide N. Angew. Chem. Int. Ed. 2012; 51: 1950
24b Murugesh V, Bruneau C, Achard M, Sahoo AR, Sharma GV. M, Suresh S. Chem. Commun. 2017; 53: 10448
24c Chen W, Ma L, Paul A, Seidel D. Nat. Chem. 2018; 10: 165

25a Sundararaju B, Achard M, Sharma GV. M, Bruneau C. J. Am. Chem. Soc. 2011; 133: 10340
25b Millet A, Larini P, Clot E, Baudoin O. Chem. Sci. 2013; 4: 2241
25c Jiang F, Achard M, Bruneau C. Chem. Eur. J. 2015; 21: 14319
25d Lee M, Sanford MS. Org. Lett. 2017; 19: 572
25e Chen M, Liu F, Dong G. Angew. Chem. Int. Ed. 2018; 57: 3815

For selected reviews, see:

26a Doye S. Angew. Chem. Int. Ed. 2001; 40: 3351
26b Campos KR. Chem. Soc. Rev. 2007; 36: 1069
26c Mitchell EA, Peschiulli A, Lefevre N, Meerpoel L, Maes BU. W. Chem. Eur. J. 2012; 18: 10092
26d Vo C.-VT, Bode JW. J. Org. Chem. 2014; 79: 2809
26e Seidel D. Acc. Chem. Res. 2015; 48: 317
26f Antermite D, Degennaro L, Luisi R. Org. Biomol. Chem. 2017; 15: 34
26g Liu G.-Q, Opatz T. Adv. Heterocycl. Chem. 2018; 125: 107
26h Gonnard L, Guérinot A, Cossy J. Tetrahedron 2019; 75: 145

For selected examples see:

27a Beak P, Kerrick ST, Wu S, Chu J. J. Am. Chem. Soc. 1994; 116: 3231
27b Campos KR, Klapars A, Waldman JH, Dormer PG, Chen C. J. Am. Chem. Soc. 2006; 128: 3538
27c Stead D, Carbone G, O’Brien P, Campos KR, Coldham I, Sanderson A. J. Am. Chem. Soc. 2010; 132: 7260
27d Beng TK, Gawley RE. J. Am. Chem. Soc. 2010; 132: 12216
27e Hodgson DM, Kloesges J. Angew. Chem. Int. Ed. 2010; 49: 2900
27f Seel S, Thaler T, Takatsu K, Zhang C, Zipse H, Straub BF, Mayer P, Knochel P. J. Am. Chem. Soc. 2011; 133: 4774
27g Cordier CJ, Lundgren RJ, Fu GC. J. Am. Chem. Soc. 2013; 135: 10946
27h Firth JD, O’Brien P, Ferris L. J. Am. Chem. Soc. 2016; 138: 651

28 Ishii Y, Chatani N, Kakiuchi F, Murai S. Organometallics 1997; 16: 3615
29 Ishii Y, Chatani N, Kakiuchi F, Murai S. Tetrahedron Lett. 1997; 38: 7565
30 Chatani N, Asaumi T, Ikeda T, Yorimistu S, Ishii Y, Kakiuchi F, Murai S. J. Am. Chem. Soc. 2000; 122: 12882
31 Pastine SJ, Gribkov DV, Sames D. J. Am. Chem. Soc. 2006; 128: 14220

32a Prokopcová H, Bergman SD, Aelvoet K, Smout V, Herrebout W, Van der Veken B, Meerpoel L, Maes BU. W. Chem. Eur. J. 2010; 16: 13063
32b Peschiulli A, Smout V, Storr TE, Mitchell EA, Eliáš Z, Herrebout W, Berthelot D, Meerpoel L, Maes BU. W. Chem. Eur. J. 2013; 19: 10378

33 Gribkov DV, Pastine SJ, Schnürch M, Sames D. J. Am. Chem. Soc. 2007; 129: 11750
34 For a systematic study and alternative conditions for pyridine removal, see: Smout V, Peschiulli A, Verbeeck S, Mitchell EA, Herrebout W, Bultinck P, Vande Velde CM. L, Berthelot D, Meerpoel L, Maes BU. W. J. Org. Chem. 2013; 78: 9803
35 Schwarz MC, Dastbaravardeh N, Kirchner K, Schnürch M, Mihovilovic MD. Monatsh. Chem. 2013; 144: 539
36 Spangler JE, Kobayashi Y, Verma P, Wang D.-H, Yu J.-Q. J. Am. Chem. Soc. 2015; 137: 11876
37 For a review of Pd^II/Pd⁰ C–H functionalization, see: Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
38 Jain P, Verma P, Xia G, Yu J.-Q. Nat. Chem. 2017; 9: 140
39 For a review on BINOL-derived phosphate ligands in asymmetric catalysis, see: Parmar D, Sugiono E, Raja S, Rueping M. Chem. Rev. 2014; 114: 9047
40 For a single example of complementary C–H arylation of tetrahydroisoquinoline at the benzylic position, see: Dastbaravardeh N, Kirchner K, Schnürch M, Mihovilovic MD. J. Org. Chem. 2013; 78: 658
41 Jiang H.-J, Zhong X.-M, Yu J, Zhang Y, Zhang X, Wu Y.-D, Gong L.-Z. Angew. Chem. Int. Ed. 2019; 58: 1803
42 Greßies S, Klauck FJ. R, Kim JH, Daniliuc CG, Glorius F. Angew. Chem. Int. Ed. 2018; 57: 9950
43 For a recent review on TADDOL-based P ligands in C–H activation reaction, see: Pedroni J, Cramer N. Chem. Commun. 2015; 51: 17647
44 Chatani N, Asaumi T, Yorimistu S, Ikeda T, Kakiuchi F, Murai S. J. Am. Chem. Soc. 2001; 123: 10935
45 Bergman SD, Storr TE, Prokopková H, Aelvoet K, Diels G, Meerpoel L, Maes BU. W. Chem. Eur. J. 2012; 18: 10393
46 MacConnell JG, Blum MS, Fales HM. Science 1970; 168: 840
47 Kulago AA, Van Steijvoort BF, Mitchell EA, Meerpoel L, Maes BU. W. Adv. Synth. Catal. 2014; 356: 1610
48 Schinkel M, Wang L, Bielefeld K, Ackermann L. Org. Lett. 2014; 16: 1876
49 Yi CS, Yun SY. Organometallics 2004; 23: 5392
50 Herzon SB, Hartwig JF. J. Am. Chem. Soc. 2007; 129: 6690
51 Eisenberger P, Ayinla RO, Lauzon JM. P, Schafer LL. Angew. Chem. Int. Ed. 2009; 48: 8361
52 Chong E, Brandt JW, Schafer LL. J. Am. Chem. Soc. 2014; 136: 10898
53 Payne PR, Garcia P, Eisenberger P, Yim JC.-H, Schafer LL. Org. Lett. 2013; 15: 2182
54 DeBoef B, Pastine SJ, Sames D. J. Am. Chem. Soc. 2004; 126: 6556
55 For a related Co-catalyzed transfer hydrogenation of various N-[(vinyl)silyl]heterocycles, see: Bolig AD, Brookhart M. J. Am. Chem. Soc. 2007; 129: 14544
56 Lahm G, Opatz T. Org. Lett. 2014; 16: 4201
57 Tahara Y, Michino M, Ito M, Kanyiva KS, Shibata T. Chem. Commun. 2015; 51: 16660
58 Tran AT, Yu J.-Q. Angew. Chem. Int. Ed. 2017; 56: 10530
59 Affron DP, Davis OA, Bull JA. Org. Lett. 2014; 16: 4956
60 Nack WA, Wang B, Wu X, Jiao R, He G, Chen G. Org. Chem. Front. 2016; 3: 561
61 Affron DP, Bull JA. Eur. J. Org. Chem. 2016; 2016: 139
62 Feng R, Wang B, Liu Y, Liu Z, Zhang Y. Eur. J. Org. Chem. 2015; 2015: 142

For the synthesis of a Pd(IV) complex as competent precatalyst see:

63a Vicente J., Arcas A., Juliá-Hernández F., Bautista D.; Angew. Chem. Int. Ed. 2011, 50, 6896.

For a DFT study on the mechanism of a related Pd-catalyzed, AQ-assisted C(sp³)–H arylation with aryl bromides, see:

63b Wei Y, Tang H, Cong X, Rao B, Wu C, Zeng X. Org. Lett. 2014; 16: 2248

64 Yang X, Sun T.-Y, Rao Y. Chem. Eur. J. 2016; 22: 3273
65 Berger M, Chauhan R, Rodrigues CA. B, Maulide N. Chem. Eur. J. 2016; 22: 16805

66a Yu Q.-Y, Zhong H.-M, Sun W.-W, Zhang S.-J, Cao P, Dong X.-P, Qin H.-B, Liu J.-K, Wu B. Asian J. Org. Chem. 2016; 5: 608
66b Zhang S.-J, Sun W.-W, Yu Q.-Y, Cao P, Dong X.-P, Wu B. Tetrahedron Lett. 2017; 58: 606

67 Hacksell U, Arvidsson LE, Svensson U, Nilsson JL. G, Sanchez D, Wikstroem H, Lindberg P, Hjorth S, Carlsson A. J. Med. Chem. 1981; 24: 1475
68 Mondal B, Roy B, Kazmaier U. J. Org. Chem. 2016; 81: 11646
69 Ye S, Yang W, Coon T, Fanning D, Neubert T, Stamos D, Yu J.-Q. Chem. Eur. J. 2016; 22: 4748
70 Maetani M, Zoller J, Melillo B, Verho O, Kato N, Pu J, Comer E, Schreiber SL. J. Am. Chem. Soc. 2017; 139: 11300
71 Kato N, Comer E, Sakata-Kato T, Sharma A, Sharma M, Maetani M, Bastien J, Brancucci NM, Bittker JA, Corey V, Clarke D, Derbyshire ER, Dornan GL, Duffy S, Eckley S, Itoe MA, Koolen KM. J, Lewis TA, Lui PS, Lukens AK, Lund E, March S, Meibalan E, Meier BC, McPhail JA, Mitasev B, Moss EL, Sayes M, Van Gessel Y, Wawer MJ, Yoshinaga T, Zeeman A.-M, Avery VM, Bhatia SN, Burke JE, Catteruccia F, Clardy JC, Clemons PA, Dechering KJ, Duvall JR, Foley MA, Gusovsky F, Kocken CH. M, Marti M, Morningstar ML, Munoz B, Neafsey DE, Sharma A, Winzeler EA, Wirth DF, Scherer CA, Schreiber SL. Nature 2016; 538: 344
72 Verho O, Maetani M, Melillo B, Zoller J, Schreiber SL. Org. Lett. 2017; 19: 4424
73 Parella R, Babu SA. J. Org. Chem. 2015; 80: 2339
74 Probst NP, Grelier G, Dahaoui S, Alami M, Gandon V, Messaoudi S. ACS Catal. 2018; 8: 7781
75 Zhang S.-Y, Li Q, He G, Nack WA, Chen G. J. Am. Chem. Soc. 2013; 135: 12135
76 Yang Q, Yang S.-D. ACS Catal. 2017; 7: 5220
77 Zhu Q, Ji D, Liang T, Wang X, Xu Y. Org. Lett. 2015; 17: 3798
78 Miao J, Yang K, Kurek M, Ge H. Org. Lett. 2015; 17: 3738

79a Sun W.-W, Cao P, Mei R.-Q, Li Y, Ma Y.-L, Wu B. Org. Lett. 2014; 16: 480
79b Zhang S.-J, Sun W.-W, Cao P, Dong X.-P, Liu J.-K, Wu B. J. Org. Chem. 2016; 81: 956

80 Heinze-Krauss I, Angehrn P, Charnas RL, Gubernator K, Gutknecht E.-M, Hubschwerlen C, Kania M, Oefner C, Page MG. P, Sogabe S, Specklin J.-L, Winkler F. J. Med. Chem. 1998; 41: 3961
81 Wasa M, Chan KS. L, Zhang X.-G, He J, Miura M, Yu J.-Q. J. Am. Chem. Soc. 2012; 134: 18570
82 He J, Wasa M, Chan KS. L, Yu J.-Q. J. Am. Chem. Soc. 2013; 135: 3387
83 Antermite D, Affron DP, Bull JA. Org. Lett. 2018; 20: 3948
84 Bourin M, Chue P, Guillon Y. CNS Drug Rev. 2001; 7: 25
85 Van Steijvoort BF, Kaval N, Kulago AA, Maes BU. W. ACS Catal. 2016; 6: 4486
86 He G, Chen G. Angew. Chem. Int. Ed. 2011; 50: 5192
87 Achan J, Talisuna AO, Erhart A, Yeka A, Tibenderana JK, Baliraine FN, Rosenthal PJ, D’Alessandro U. Malar. J. 2011; 10: 144
88 O’Donovan DH, Aillard P, Berger M, de la Torre A, Petkova D, Knittl-Frank C, Geerdink D, Kaiser M, Maulide N. Angew. Chem. Int. Ed. 2018; 57: 10737

89a Willcox D, Chappell BG. N, Hogg KF, Calleja J, Smalley AP, Gaunt MJ. Science 2016; 354: 851
89b Hogg KF, Trowbridge A, Alvarez-Pérez A, Gaunt MJ. Chem. Sci. 2017; 8: 8198
89c Cabrera-Pardo JR, Trowbridge A, Nappi M, Ozaki K, Gaunt MJ. Angew. Chem. Int. Ed. 2017; 56: 11958

90 Topczewski JJ, Cabrera PJ, Saper NI, Sanford MS. Nature 2016; 531: 220
91 Beer B, Stark J, Krieter P, Czobor P, Beer G, Lippa A, Skolnick P. J. Clin. Pharmacol. 2004; 44: 1360
92 Coe JW, Brooks PR, Vetelino MG, Wirtz MC, Arnold EP, Huang J, Sands SB, Davis TI, Lebel LA, Fox CB, Shrikhande A, Heym JH, Schaeffer E, Rollema H, Lu Y, Mansbach RS, Chambers LK, Rovetti CC, Schulz DW, Tingley FD, O’Neill BT. J. Med. Chem. 2005; 48: 3474
93 Walker N, Howe C, Glover M, McRobbie H, Barnes J, Nosa V, Parag V, Bassett B, Bullen C. N. Engl. J. Med. 2014; 371: 2353
94 Dewyer AL, Zimmerman PM. ACS Catal. 2017; 7: 5466
95 Aguilera EY, Sanford MS. Organometallics 2019; 38: 138
96 Cabrera PJ, Lee M, Sanford MS. J. Am. Chem. Soc. 2018; 140: 5599