Recent Developments in Photochemical and Electrochemical Decarboxylative C(sp3)–N Bond Formation

Yue Zheng; Xiaoqing Shao; Velayudham Ramadoss; Lifang Tian; Yahui Wang

doi:10.1055/s-0039-1690839

Synthesis, Table of Contents

Synthesis 2020; 52(09): 1357-1368
DOI: 10.1055/s-0039-1690839

short review

Recent Developments in Photochemical and Electrochemical Decarboxylative C(sp³)–N Bond Formation

Yue Zheng

,

Xiaoqing Shao

,

Velayudham Ramadoss

,

Lifang Tian∗

Institute of Advanced Synthesis (IAS), School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, P. R. of China Email: tianlifang@njtech.edu.cn Email: ias_yhwang@njtech.edu.cn

,

Yahui Wang∗

Institute of Advanced Synthesis (IAS), School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, P. R. of China Email: tianlifang@njtech.edu.cn Email: ias_yhwang@njtech.edu.cn

› Author Affiliations

Abstract

All articles of this category

Dedicated to Professor Antonio M. Echavarren on the occasion of his 65^th birthday

Abstract

Considering the important applications of nitrogen-containing compounds in agrochemical materials and biomolecular drug molecules, research on methods for the construction of C–N bonds quickly and efficiently has become an important topic in synthetic chemistry. Carboxylic acids are inexpensive, stable, and non-toxic substances that are widely present in Nature, which makes them appealing as potential coupling partners for C(sp³)–N bond-forming reactions. Moreover, compared with the well-established transition-metal-catalyzed protocols, the rapid development of photoredox catalysis and electrochemical methods in recent years provides options for chemists to design new synthetic routes. In this short review, we concentrate on the decarboxylative C(sp³)–N coupling reactions mediated by visible light or electricity, with special attention on mechanistic insights.

1 Introduction

2 Photoredox-Mediated Decarboxylative C(sp³)–N Bond Formation

2.1 Intramolecular Decarboxylation

2.2 Intermolecular Decarboxylation

3 Electrochemistry-Induced Decarboxylative C(sp³)–N Bond Formation

3.1 Intramolecular Decarboxylation

3.2 Intermolecular Decarboxylation

4 Conclusions and Outlook

Key words

decarboxylation - C–N bonds - cross-coupling - photochemistry - electrochemistry

Full Text

References

References

1a Vitaku E, Smith DT, Njardarson JT. J. Med. Chem. 2014; 57: 10257
1b Top 200 Small Molecule Pharmaceuticals by Retail Sales in 2018, Compiled and Produced by the Njarðarson Group, University of Arizona (https://njardarson.lab.arizona.edu/content/top-pharmaceuticals-poster), see: McGrath NA, Brichacek M, Njardarson JT. J. Chem. Educ. 2010; 87: 1348
1c Urieta-Mora J, Garcia-Benito I, Molina-Ontoria A, Martin N. Chem. Soc. Rev. 2018; 47: 8541
1d Luo J, Wei W.-T. Adv. Synth. Catal. 2018; 360: 2076
1e Song S.-Z, Dong Y, Ge G.-P, Li Q, Wei W.-T. Synthesis 2020; 52: in press; DOI: 10.1055/s0039-1690789

2a Beletskaya IP, Cheprakov AV. Organometallics 2012; 31: 7753
2b Bariwal J, Van der Eycken E. Chem. Soc. Rev. 2013; 42: 9283

3a Hartwig JF. Acc. Chem. Res. 2008; 41: 1534
3b Ruiz-Castillo P, Buchwald SL. Chem. Rev. 2016; 116: 12564

4a Monnier F, Taillefer M. Angew. Chem. Int. Ed. 2009; 48: 6954
4b Creutz SE, Lotito KJ, Fu GC, Peters JC. Science 2012; 338: 647
4c Sambiagio C, Marsden SP, Blacker AJ, McGowan PC. Chem. Soc. Rev. 2014; 43: 3525

5 Qiao JX, Lam PY. S. Synthesis 2011; 829

6a Hu X. Chem. Sci. 2011; 2: 1867
6b Tasker SZ, Standley EA, Jamison TF. Nature 2014; 509: 299
6c Choi J, Fu GC. Science 2017; 356: eaaf7230

7 Advanced Organic Chemistry, Part B: Reactions and Synthesis, 5th ed. Carey FA, Sundberg RJ. Springer, Science+Business Media LLC; New York: 2007: 229-232
8 Gomez S, Peters JA, Maschmeyer T. Adv. Synth. Catal. 2002; 344: 1037
9 Ghosh AK, Brindisi M, Sarkar A. ChemMedChem 2018; 13: 2351
10 Swamy KC. K, Kumar NN. B, Balaraman E, Kumar KV. P. P. Chem. Rev. 2009; 109: 2551

11a Arndtsen BA, Bergman RG, Mobley TA, Peterson TH. Acc. Chem. Res. 1995; 28: 154
11b Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
11c Colby DA, Bergman RG, Ellman JA. Chem. Rev. 2010; 110: 624
11d Mkhalid IA. I, Barnard JH, Marder TB, Murphy JM, Hartwig JF. Chem. Rev. 2010; 110: 890
11e Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147

12 Johnson RG, Ingham RK. Chem. Rev. 1956; 56: 219
13 Saraiva MF, Couri MR. C, Hyaric ML, de Almeida MV. Tetrahedron 2009; 65: 3563

14a Rodríguez N, Goossen LJ. Chem. Soc. Rev. 2011; 40: 5030
14b Weaver JD, Recio A, Grenning AJ, Tunge JA. Chem. Rev. 2011; 111: 1846
14c Cornella J, Larrosa I. Synthesis 2012; 44: 653
14d Xuan J, Zhang Z.-G, Xiao W.-J. Angew. Chem. Int. Ed. 2015; 54: 15632
14e Wei Y, Hu P, Zhang M, Su W. Chem. Rev. 2017; 117: 8864
14f Schwarz J, Konig B. Green Chem. 2018; 20: 323
14g Arshadi S, Ebrahimiasl S, Hosseinian A, Monfared A, Vessally E. RSC Adv. 2019; 9: 8964
14h Rahman M, Mukherjee A, Kovalev IS, Kopchuk DS, Zyryanov GV, Tsurkan MV, Majee A, Ranu BC, Charushin VN, Chupakhin ON, Santra S. Adv. Synth. Catal. 2019; 361: 2161
14i Moon PJ, Lundgren RJ. ACS Catal. 2020; 10: 1742
14j Daley RA, Topczewski JJ. Synthesis 2020; 52: 365

15a Kiyokawa K, Yahata S, Kojima T, Minakata S. Org. Lett. 2014; 16: 4646
15b Liu C, Wang X, Li Z, Cui L, Li C. J. Am. Chem. Soc. 2015; 137: 9820
15c Zhu Y, Li X, Wang X, Huang X, Shen T, Zhang Y, Sun X, Zou M, Song S, Jiao N. Org. Lett. 2015; 17: 4702
15d Liu Z.-J, Lu X, Wang G, Li L, Jiang W.-T, Wang Y.-D, Xiao B, Fu Y. J. Am. Chem. Soc. 2016; 138: 9714
15e Fang Z, Feng Y, Dong H, Li D, Tang T. Chem. Commun. 2016; 52: 11120
15f Kong D, Moon PJ, Bsharat O, Lundgren RJ. Angew. Chem. Int. Ed. 2020; 59: 1313

16a Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322
16b Welin ER, Le C, Arias-Rotondo DM, McCusker JK, MacMillan DW. C. Science 2017; 355: 380
16c Le C, Liang Y, Evans RW, Li X, MacMillan DW. C. Nature 2017; 547: 79

17 Romero NA, Nicewicz DA. Chem. Rev. 2016; 116: 10075

18a Grabowski ZR, Rotkiewicz K, Rettig W. Chem. Rev. 2003; 103: 3899
18b Shaw MH, Twilton J, MacMillan DW. C. J. Org. Chem. 2016; 81: 6898

19a Huang H, Jia K, Chen Y. ACS Catal. 2016; 6: 4983
19b Zuo Z, Ahneman DT, Chu L, Terrett JA, Doyle AG, MacMillan DW. C. Science 2014; 345: 437
19c Johnston CP, Smith RT, Allmendinger S, MacMillan DW. C. Nature 2016; 536: 322

20a Yan M, Kawamata Y, Baran PS. Chem. Rev. 2017; 117: 13230
20b Zhao Y, Xia W. Chem. Soc. Rev. 2018; 47: 2591
20c Karkas MD. Chem. Soc. Rev. 2018; 47: 5786
20d Jiang Y, Xu K, Zeng C. Chem. Rev. 2018; 118: 4485
20e Mohle S, Zirbes M, Rodrigo E, Gieshoff T, Wiebe A, Waldvogel SR. Angew. Chem. Int. Ed. 2018; 57: 6018
20f Lei A, Yuan Y. Acc. Chem. Res. 2019; 52: 3309
20g Xiong P, Xu H.-C. Acc. Chem. Res. 2019; 52: 3339
20h Leech MC, Lam K. Acc. Chem. Res. 2020; 53: 121
20i Yamamoto K, Kuriyama M, Onomura O. Acc. Chem. Res. 2020; 53: 105
20j Ackermann L. Acc. Chem. Res. 2020; 53: 84

21a Klocke E, Matzeit A, Gockeln M, Schafer HJ. Chem. Ber. 1993; 126: 1623
21b Comprehensive Organic Name Reactions and Reagents . Wang Z. John Wiley & Sons; Hoboken: 2009: 1443-1446

22a Torii S. In Electroorganic Syntheses: Methods and Applications, Part 1: Oxidations (Monographs in Modern Chemistry). Ebel HF. Kodansha; Tokyo: 1985
22b Schafer HJ. Top. Curr. Chem. 1990; 152: 91

23 Xiang J, Shang M, Kawamata Y, Lundberg H, Reisberg S, Chen M, Mykhailiuk P, Beutner G, Collins M, Davies A, Bel MD, Gallego G, Spangler J, Starr JT, Yang S, Blackmond D, Baran PS. Nature 2019; 573: 398
24 Yoshimi Y. J. Photochem. Photobiol. A 2017; 342: 116

25a Okada K, Okamoto K, Oda M. J. Am. Chem. Soc. 1988; 110: 8736
25b Okada K, Okamoto K, Morita N, Okubo K, Oda M. J. Am. Chem. Soc. 1991; 113: 9401

26a Cornella J, Edwards JT, Qin T, Kawamura S, Wang J, Pan C.-M, Gianatassio R, Schmidt M, Eastgate MD, Baran PS. J. Am. Chem. Soc. 2016; 138: 2174
26b Qin T, Cornella J, Li C, Malins LR, Edwards JT, Kawamura S, Maxwell BD, Eastgate MD, Baran PS. Science 2016; 352: 801
26c Toriyama F, Cornella J, Wimmer L, Chen T.-G, Dixon DD, Creech G, Baran PS. J. Am. Chem. Soc. 2016; 138: 11132
26d Jin Y, Yang H, Fu H. Chem. Commun. 2016; 52: 12909
26e Edwards JT, Merchant RR, McClymont KS, Knouse KW, Qin T, Malins LR, Vokits B, Shaw SA, Bao D.-H, Wei F.-L, Zhou T, Eastgate MD, Baran PS. Nature 2017; 545: 213
26f Huang L, Olivares AM, Weix DJ. Angew. Chem. Int. Ed. 2017; 56: 11901
26g Liu Y, Xue L, Shi B, Bu F, Wang D, Lu L, Shi R, Lei A. Chem. Commun. 2019; 55: 14922
26h Guo J.-Y, Zhang Z.-Y, Guan T, Mao L.-W, Ban Q, Zhao K, Loh T.-P. Chem. Sci. 2019; 10: 8792

27a Mao R, Balon J, Hu X. Angew. Chem. Int. Ed. 2018; 57: 13624
27b Jin S, Haug GC, Nguyen VT, Flores-Hansen C, Arman HD, Larionov OV. ACS Catal. 2019; 9: 9764
27c Shibutani S, Kodo T, Takeda M, Nagao K, Tokunaga N, Sasaki Y, Ohmiya H. J. Am. Chem. Soc. 2020; 142: 1211

28a Li C, Wang J, Barton LM, Yu S, Tian M, Peters DS, Kumar M, Yu AW, Johnson KA, Chatterjee AK, Yan M, Baran PS. Science 2017; 356: 7355
28b Fawcett A, Pradeilles J, Wang Y, Mutsuga T, Myers EL, Aggarwal VK. Science 2017; 357: 283
28c Candish L, Teders M, Glorius F. J. Am. Chem. Soc. 2017; 139: 7440
28d Hu D, Wang L, Li P. Org. Lett. 2017; 19: 2770
28e Xue W, Oestreich M. Angew. Chem. Int. Ed. 2017; 56: 11649

29 Zhao W, Wurz RP, Peters JC, Fu GC. J. Am. Chem. Soc. 2017; 139: 12153
30 Kiyokawa K, Watanabe T, Fra L, Kojima T, Minakata S. J. Org. Chem. 2017; 82: 11711

31a Guérinot A, Reymond S, Cossy J. Eur. J. Org. Chem. 2012; 19
31b Jiang D, He T, Ma L, Wang Z. RSC Adv. 2014; 4: 64936

32 Kiyokawa K, Takemoto K, Minakata S. Chem. Commun. 2016; 52: 13082
33 Mao R, Frey A, Balon J, Hu X. Nat. Catal. 2018; 1: 120
34 Jamison CR, Overman LE. Acc. Chem. Res. 2016; 49: 1578
35 Zhang H, Zhang P, Jiang M, Yang H, Fu H. Org. Lett. 2017; 19: 1016
36 Liang Y, Zhang X, MacMillan DW. C. Nature 2018; 559: 83
37 Lowry MS, Goldsmith JI, Slinker JD, Rohl R, Pascal RA, Malliaras GG, Bernhard S. Chem. Mater. 2005; 17: 5712
38 Tran BL, Li B, Driess M, Hartwig JF. J. Am. Chem. Soc. 2014; 136: 2555
39 Sakakibara Y, Ito E, Fukushima T, Murakami K, Itami K. Chem. Eur. J. 2018; 24: 9254
40 Ito E, Fukushima T, Kawakami T, Murakami K, Itami K. Chem 2017; 2: 383
41 Marcote DC, Street-Jeakings R, Dauncey E, Douglas JJ, Ruffoni A, Leonori D. Org. Biomol. Chem. 2019; 17: 1839

42a Hopkinson MN, Sahoo B, Li J.-L, Glorius F. Chem. Eur. J. 2014; 20: 3874
42b Skubi KL, Blum TR, Yoon TP. Chem. Rev. 2016; 116: 10035

43a Zhdankin VV, Krasutsky AP, Kuehl CJ, Simonsen AJ, Woodward JK, Mismash B, Bolz JT. J. Am. Chem. Soc. 1996; 118: 5192
43b Weidner K, Renaud P. Aust. J. Chem. 2013; 66: 341

44 Seebach D, Charczuk R, Gerber C, Renaud P, Berner H, Schneider H. Helv. Chim. Acta 1989; 72: 401
45 Thomas HG. Angew. Chem. Int. Ed. 1971; 10: 557

46a Yoshida J.-i, Suga S, Suzuki S, Kinomura N, Yamamoto A, Fujiwara K. J. Am. Chem. Soc. 1999; 121: 9546
46b Shoji T, Kim S, Chiba K. Angew. Chem. Int. Ed. 2017; 56: 4011
46c Yoshida J.-i, Shimizu A, Hayashi R. Chem. Rev. 2018; 118: 4702
46d Shao X, Tian L, Wang Y. Eur. J. Org. Chem. 2019; 4089
46e Xu Z, Zheng Y, Wang Z, Shao X, Tian L, Wang Y. Chem. Commun. 2019; 55: 15089
46f Yang Y.-Z, Song R.-J, Li J.-H. Org. Lett. 2019; 21: 3228

47 Shao X, Zheng Y, Tian L, Torres IM, Echavarren AM, Wang Y. Org. Lett. 2019; 21: 9262

48a Shida N, Zhou Y, Inagi S. Acc. Chem. Res. 2019; 52: 2598
48b Noel T, Cao Y, Laudadio G. Acc. Chem. Res. 2019; 52: 2858

49 Yu Y, Guo P, Zhong J.-S, Yuan Y, Ye K.-Y. Org. Chem. Front. 2020; 7: 131