Recent Progress on Copper-Catalyzed C–C Bond Formation via C(sp2)–H Insertions Using Diazo and Related Compounds

Satabdi Bera; Subhenira Jana; Rajarshi Samanta

doi:10.1055/a-2134-0352

Synthesis, Inhaltsverzeichnis

Synthesis 2024; 56(01): 29-46
DOI: 10.1055/a-2134-0352

short review

Recent Progress on Copper-Catalyzed C–C Bond Formation via C(sp²)–H Insertions Using Diazo and Related Compounds

Satabdi Bera

,

Subhenira Jana

,

Rajarshi Samanta∗

Abstract

Alle Artikel dieser Rubrik

Abstract

The site-selective insertion of metal carbenes via C(sp²)–H bond functionalization is an interesting topic within the synthetic chemistry community. In recent years, studies on the formation and applications of copper carbene intermediates have increased significantly due to their cost-effectiveness and versatile reactivities. Furthermore, copper-catalyzed transformations involving C(sp²)–H insertions using diazo and related compounds, along with asymmetric versions, have emerged as new tools for C–C bond formation. This short review summarizes selected recent advances in this field.

1 Introduction

2 Insertion of Copper Carbenes into Aryl C(sp²)–H Bonds of Arenes

3 Copper Carbene Insertion into Aryl C(sp²)–H Bonds of Azaheteroarenes

4 Copper Carbene Insertion into C(sp²)–H Bonds of Alkenes

5 Conclusions and Perspectives

Key words

copper catalysis - metal carbenes - C(sp²)–H insertion - C–C bond - diazo compounds

Volltext

Referenzen

References

1a Zheng Z, Wang Z, Wang Y, Zhang L. Chem. Soc. Rev. 2016; 45: 4448
1b Zhang L. Acc. Chem. Res. 2014; 47: 877
1c Asiri AM, Hashmi AS. K. Chem. Soc. Rev. 2016; 45: 4471
1d Obradors C, Echavarren AM. Acc. Chem. Res. 2014; 47: 902
1e Zi W, Toste FD. Chem. Soc. Rev. 2016; 45: 4567

2 Silberrad O, Roy CS. J. Chem. Soc. Trans. 1906; 89: 179

3a Nozaki H, Moriuti S, Yamabe M, Noyori R. Tetrahedron Lett. 1966; 7: 59
3b Nozaki H, Takaya H, Moriuti S, Noyori R. Tetrahedron 1968; 24: 3655
3c Dauben WG, Hendricks RT, Luzzio MJ, Ng HP. Tetrahedron Lett. 1990; 31: 6969

4a Lowenthal RE, Abiko A, Masamune S. Tetrahedron Lett. 1990; 31: 6005
4b Evans DA, Woerpel KA, Hinman MM, Faul MM. J. Am. Chem. Soc. 1991; 113: 726
4c Evans DA, Woerpel KA, Scott MJ. Angew. Chem. Int. Ed. 1992; 31: 430
4d Pfaltz A. Acc. Chem. Res. 1993; 26: 339
4e Díaz-Requejo MM, Pérez PJ. J. Organomet. Chem. 2001; 617: 110
4f Straub BF, Hofmann P. Angew. Chem. Int. Ed. 2001; 40: 1288
4g Fraile JM, García JI, Martínez-Merino V, Mayoral JA, Salvatella L. J. Am. Chem. Soc. 2001; 123: 7616
4h Liao S, Sun XL, Tang Y. Acc. Chem. Res. 2014; 47: 2260
4i Xie JH, Zhu QL. Acc. Chem. Res. 2008; 41: 581
4j Peris E. Chem. Rev. 2018; 118: 9988

5a Diaz-Requejo MM, Belderrain TR, Nicasio MC, Trofimenko S, Pérez PJ. J. Am. Chem. Soc. 2002; 124: 896
5b Flynn CJ, Elcoate CJ, Lawrence SE, Maguire AR. J. Am. Chem. Soc. 2010; 132: 1184
5c Carreras V, Besnard C, Gandon V, Ollevier T. Org. Lett. 2019; 21: 9094
5d Zhang YZ, Zhu SF, Wang LX, Zhou QL. Angew. Chem. Int. Ed. 2008; 47: 8496
5e Maier TC, Fu GC. J. Am. Chem. Soc. 2006; 128: 4594
5f Morilla ME, Molina MJ, Diaz-Requejo MM, Belderrain TR, Nicasio MC, Trofimenko S, Pérez PJ. Organometallics 2003; 22: 2914

6a Xu H, Li Y, Cai Y, Wang G, Zhu SF, Zhou QL. J. Am. Chem. Soc. 2017; 139: 7697
6b Noyori R, Takaya H, Nakanisi Y, Nozaki H. Can. J. Chem. 1969; 47: 1242

7a Huang Y, Li X, Wang X, Yu Y, Zheng J, Wu W, Jiang H. Chem. Sci. 2017; 8: 7047
7b Dong K, Pei C, Zeng Q, Qiu L, Hu W, Qian Y, Xu X. Chem. Commun. 2019; 55: 6393
7c Luo H, He C, Jiang H, Zhu S. Chin. J. Chem. 2020; 38: 1052

8a Qu J, Xu Z, Zhou J, Cao C, Sun X, Dai L, Tang Y. Adv. Synth. Catal. 2009; 351: 308
8b Alavala GK, Sajjad F, Shi T, Kang Z, Ma M, Xing D, Hu W. Chem. Commun. 2018; 54: 12650
8c Nair VN, Kojasoy V, Laconsay CJ, Kong WY, Tantillo DJ, Tambar UK. J. Am. Chem. Soc. 2021; 143: 9016

9a Zeng Q, Dong K, Pei C, Dong S, Hu W, Qiu L, Xu X. ACS Catal. 2019; 9: 10773
9b Pei C, Rong GW, Yu ZX, Xu X. J. Org. Chem. 2018; 83: 13243

10a Marichev KO, Wang K, Dong K, Greco N, Massey LA, Deng Y, Arman H, Doyle MP. Angew. Chem. Int. Ed. 2019; 58: 16188
10b Marichev KO, Dong K, Massey LA, Deng Y, Angelis L, Wang K, Arman H, Doyle MP. Nat. Commun. 2019; 10: 5328
10c Marichev KO, Doyle MP. Org. Biomol. Chem. 2019; 17: 4183

11a Yang JM, Li ZQ, Li ML, He Q, Zhu SF, Zhou QL. J. Am. Chem. Soc. 2017; 139: 3784
11b Zhu S, Zhou QL. Acc. Chem. Res. 2012; 45: 1365

12a Xia Y, Wang J. J. Am. Chem. Soc. 2020; 142: 10592
12b Xia Y, Qiu D, Wang J. Chem. Rev. 2017; 117: 13810
12c Xia Y, Wang J. Chem. Soc. Rev. 2017; 46: 2306

13a Álvarez M, Besora M, Molina F, Maseras F, Belderrain TR, Pérez PJ. J. Am. Chem. Soc. 2021; 143: 4837
13b Rodríguez AM, Molina F, Díaz-Requejo MM, Pérez PJ. Adv. Synth. Catal. 2020; 362: 1998

14a Davies HM. L, Hedley SJ. Chem. Soc. Rev. 2007; 36: 1109
14b Alford JS, Davies HM. L. Chem. Soc. Rev. 2014; 43: 5151

15 Zhao X, Zhang Y, Wang J. Chem. Commun. 2012; 48: 10162
16 Kirmse W. Angew. Chem. Int. Ed. 2003; 42: 1088
17 Dong K, Liu M, Xu X. Molecules 2022; 27: 3088

18a Yamaguchi J, Yamaguchi AD, Itami K. Angew. Chem. Int. Ed. 2012; 51: 8960
18b Ackermann L. Org. Process Res. Dev. 2015; 19: 260
18c Mercier LG, Leclerc M. Acc. Chem. Res. 2013; 46: 1597
18d Ackermann L. Chem. Rev. 2011; 111: 1315
18e Willis MC. Chem. Rev. 2010; 110: 725
18f Dobereiner GE, Crabtree RH. Chem. Rev. 2010; 110: 681
18g Gunay A, Theopold KH. Chem. Rev. 2010; 110: 1060
18h Kakiuchi F, Kochi T. Synthesis 2008; 19: 3013
18i Priyanka Sharma RK, Katiyar D. Synthesis 2016; 48: 2303

19a Hu F, Xia Y, Ma C, Zhang Y, Wang J. Chem. Commun. 2015; 51: 7986
19b Davies HM. L, Beckwith RE. J. Chem. Rev. 2003; 103: 2861
19c Davies HM. L, Manning JR. Nature 2008; 451: 417
19d Gao X, Wu B, Yan Z, Zhou YZ. Org. Biomol. Chem. 2016; 14: 8237
19e Wu JQ, Yang Z, Zhang SS, Jiang CY, Li Q, Huang ZS, Wang H. ACS Catal. 2015; 5: 6453
19f Chen X, Hu X, Bai S, Deng Y, Jiang H, Zeng W. Org. Lett. 2016; 18: 192
19g Jeong J, Patel P, Hwang H, Chang S. Org. Lett. 2014; 16: 4598
19h Ai W, Yang X, Wu Y, Wang X, Li Y, Yang Y, Zhou B. Chem. Eur. J. 2014; 20: 17653
19i Wang L, Li Z, Qu X, Peng WM, Hu SQ, Wang HB. Tetrahedron Lett. 2015; 56: 6214

Selected recent references:

20a Hu F, Xia Y, Ye F, Liu Z, Ma C, Zhang Y, Wang J. Angew. Chem. Int. Ed. 2014; 53: 1364 ; Angew. Chem. 2014, 126, 1388
20b Liang Y, Yu K, Li B, Xu S, Song H, Wang B. Chem. Commun. 2014; 50: 6130
20c Son J.-Y, Kim S, Jeon WH, Lee PH. Org. Lett. 2015; 17: 2518
20d Yu S, Liu S, Lan Y, Wan B, Li X. J. Am. Chem. Soc. 2015; 137: 1623
20e Zhou B, Chen Z, Yang Y, Ai W, Tang H, Wu Y, Zhu W, Li Y. Angew. Chem. Int. Ed. 2015; 54: 12121
20f Yang Y, Wang X, Li Y, Zhou B. Angew. Chem. Int. Ed. 2015; 54: 15400 Angew. Chem. 2015, 127, 15620
20g Mishra NK, Choi M, Jo H, Oh Y, Sharma S, Han SH, Jeong T, Han S, Lee SY, Kim IS. Chem. Commun. 2015; 51: 17229
20h Shi J, Zhou J, Yan Y, Jia J, Liu X, Song H, Xu HE, Yi W. Chem. Commun. 2015; 51: 668
20i Qi Z, Yu S, Li X. Org. Lett. 2016; 18: 700
20j Dateer RB, Chang S. Org. Lett. 2016; 18: 68
20k Shi P, Wang L, Guo S, Chen K, Wang J, Zhu J. Org. Lett. 2017; 19: 4359
20l Yan SY, Ling PX, Shi BF. Adv. Synth. Catal. 2017; 359: 2912
20m Long Z, Wang Z, Zhou D, Wan D, You J. Org. Lett. 2017; 19: 2777

21 Tayama E, Yanaki T, Iwamoto H, Hasegawa E. Eur. J. Org. Chem. 2010; 6719
22 Tayama E, Ishikawa M, Iwamoto H, Hasegawa E. Tetrahedron Lett. 2012; 53: 5159
23 Gao L, Liu S, Wang ZC, Mao Y, Shi SL. Asian J. Org. Chem. 2022; 11: e202100723
24 Yang Z, Pei C, Koenigs RM. Org. Lett. 2020; 22: 7234

25a Malátková P, Wsól V. Drug Metab. Rev. 2014; 46: 96
25b Magueur G, Crousse B, Ourévitch M, Bonnet-Delpon D, Bégué J.-P. J. Fluorine Chem. 2006; 127: 637
25c Leriche C, He X, Chang TC, Liu H.-W. J. Am. Chem. Soc. 2003; 125: 6348

26 Hatakeyama T, Kondo Y, Fujiwara Y, Takaya H, Ito S, Nakamura E, Nakamura M. Chem. Commun. 2009; 1216
27 Fan S, He CY, Zhang X. Chem. Commun. 2010; 46: 4926
28 Xu S, Wu G, Ye F, Wang X, Li H, Zhao X, Zhang Z, Wang J. Angew. Chem. Int. Ed. 2015; 54: 4669
29 Ma B, Tang Z, Zhang J, Liu L. Chem. Commun. 2020; 56: 9485

30a Shao R. Curr. Mol. Pharmacol. 2008; 1: 50
30b Maretina IA, Trofimov AB. Russ. Chem. Rev. 2006; 75: 825
30c Kadela-Tomanek M, Bębenek E, Chrobak E, Latocha M, Boryczka S. Molecules 2017; 22: 447

31a Hamann PR, Upeslacis J, Borders DB. Enediynes . In Anticancer Agents from Natural Products, 2nd ed. Cragg GM, Kingston DG, Newman ID. J. CRC Press; Boca Raton (FL, USA): 2011: 575-621
31b Marsault E, Peterson ML. J. Med. Chem. 2011; 54: 1961
31c Driggers EM, Hale SP, Lee J, Terrett NK. Nat. Rev. Drug Discovery 2008; 7: 608
31d Gampe CM, Carreira EM. Angew. Chem. Int. Ed. 2012; 51: 3766

32a Zhang W, Moore JS. Angew. Chem. Int. Ed. 2006; 45: 4416
32b Kar M, Basak A. Chem. Rev. 2007; 107: 2861
32c Iyoda M, Yamakawa J, Rahman MJ. Angew. Chem. Int. Ed. 2011; 50: 10522
32d Smith MK, Miljanić OŠ. Org. Biomol. Chem. 2015; 13: 7841
32e Tahara K, Lei S. Chem. Commun. 2010; 46: 8507

33a Pei C, Zhang C, Qian Y, Xu X. Org. Biomol. Chem. 2018; 16: 8677
33b Archambeau A, Miege F, Meyer C, Cossy J. Acc. Chem. Res. 2015; 48: 1021
33c Zheng Y, Mao J, Weng Y, Zhang X, Xu X. Org. Lett. 2015; 17: 5638
33d Zeng Q, Dong K, Huang J, Qiu L, Xu X. Org. Biomol. Chem. 2019; 17: 2326

34 Carreras J, Popowski Y, Caballero A, Amir E, Perez PJ. J. Org. Chem. 2018; 83: 11125

35a Iqbal K, Jamal Q, Iqbal J, Sadaf Afreen M, Sandhu MZ. A, Dar E, Farooq U, Mushtaq MF, Arshad N, Iqbal MM. Trop. J. Pharm. Res. 2017; 16: 337
35b Deng Y, Sun C, Hunt DK, Fyfe C, Chen C.-L, Grossman TH, Sutcliffe JA, Xiao X.-Y. J. Med. Chem. 2017; 60: 2498
35c Narsimha S, Battula K, Reddy NV. Synth. Commun. 2017; 47: 928

36 Çavus MS, Gür M, Nesrin S. J. Mol. Struct. 2017; 1139: 111

37a Molnar M, Pavić V, Šarkanj B, Čačić M, Vuković D, Klenkar J. Heterocycl. Commun. 2017; 23: 35
37b Chitra C, Sudarsan S, Sakthivel S, Guhanathan S. Int. J. Biol. Macromol. 2017; 95: 363
37c Wahbi HI, Ishak CY, Khalid A, Adlan T. Int. J. Pharm. Phytopharmacol. Res. 2014; 4: 13

38a Putta RR, Donthamsetty V S, Guda DR, Adivireddy P, Padmavathi V. J. Heterocycl. Chem. 2017; 4: 2216
38b Ferrand G, Dumas H, Depin JC, Quentin Y. Eur. J. Med. Chem. 1996; 31: 273

39a Ana SF, Luminita B. Mol. Diversity 2017; 21: 437
39b Wang W, Zhou Y, Peng H, He H, Lu X. J. Fluorine Chem. 2017; 193: 8

40a Liu Y, Qing L, Meng C, Shi J, Yang Y, Wang Z, Han G, Wang Y, Ding J, Meng L.-H, Wang Q. J. Med. Chem. 2017; 60: 2764
40b Morsy SA, Farahat AA, Nasr MN. A, Tantawy AS. Saudi Pharm. J. 2017; 25: 873
40c Thigulla Y, Kumar TU, Trivedi P, Ghosh B. ChemistrySelect 2017; 7: 2721

41 Jha AK, Jain N. Chem. Commun. 2016; 52: 1831
42 Biswas A, Karmakar U, Pal A, Samanta R. Chem. Eur. J. 2016; 22: 13826
43 Monreal-Corona R, Díaz-Jiménez A, Roglans A, Poater A, Pla-Quintana A. Adv. Synth. Catal. 2023; 365: 760
44 Johansen MB, Kerr MA. Org. Lett. 2010; 12: 4956
45 Delgado-Rebollo M, Prieto A, Pérez PJ. ChemCatChem 2014; 6: 2047

46a Cheng Q.-Q, Deng Y, Lankelma M, Doyle MP. Chem. Soc. Rev. 2017; 46: 5425
46b Padwa A. Chem. Soc. Rev. 2009; 38: 3072
46c Xu X, Doyle MP. Acc. Chem. Res. 2014; 47: 1396

47a Meloche JL, Ashfeld BL. A. Angew. Chem. Int. Ed. 2017; 56: 6604
47b Rodriguez KX, Kaltwasser N, Toni TA, Ashfeld BL. Org. Lett. 2017; 19: 2482
47c Rodriguez KX, Pilato TC, Ashfeld BL. Chem. Sci. 2018; 9: 3221

48 Bhat A, Tucker N, Lin J.-B, Grover H. Chem. Commun. 2021; 57: 10556
49 Zhao X, Wu G, Zhang Y, Wang Z. J. Am. Chem. Soc. 2011; 133: 3296
50 Lonka MR, Zhang J, Gogula T, Zou H. Org. Biomol. Chem. 2019; 17: 7455

51a Kozlowski MC, Morgan BJ, Linton EC. Chem. Soc. Rev. 2009; 38: 3193
51b Carroll MP, Guiry PJ. Chem. Soc. Rev. 2014; 43: 819
51c Kumarasamy E, Raghunathan R, Sibi MP, Sivaguru J. Chem. Rev. 2015; 115: 11239

Selected literature:

52a Lim AD, Codelli JA, Reisman SE. Chem. Sci. 2013; 4: 650
52b Knöpfel TF, Zarotti P, Ichikawa T, Carreira EM. J. Am. Chem. Soc. 2005; 127: 9682
52c Rokade BV, Guiry PJ. ACS Catal. 2017; 7: 2334
52d Knöpfel TF, Aschwanden P, Ichikawa T, Watanabe T, Carreira EM. Angew. Chem. Int. Ed. 2004; 43: 5971

53 Biswas A, Pan S, Samanta R. Org. Lett. 2022; 24: 1631
54 Zhou Q, Li S, Zhang Y, Wang J. Angew. Chem. Int. Ed. 2017; 56: 16013