Transition-Metal-Catalyzed Intermolecular C–H Carbonylation toward Amides

Yan-Lin Li; Zheng-Yang Gu; Ji-Bao Xia

doi:10.1055/s-0040-1706416

Synlett, Inhaltsverzeichnis

Synlett 2021; 32(01): 07-13
DOI: 10.1055/s-0040-1706416

synpacts

Transition-Metal-Catalyzed Intermolecular C–H Carbonylation toward Amides

Yan-Lin Li

^aState Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, P. R. of China eMail: jibaoxia@licp.cas.cn

^bUniversity of Chinese Academy of Sciences, Beijing 100049, P. R. of China

,

Zheng-Yang Gu

^aState Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, P. R. of China eMail: jibaoxia@licp.cas.cn

^cCollege of Textiles and Clothing and Key Laboratory for Advanced Technology in Environmental Protection of Jiangsu Province, Yancheng Institute of Technology, Jiangsu, 224003, P. R. of China

,

Ji-Bao Xia ∗

^aState Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, P. R. of China eMail: jibaoxia@licp.cas.cn

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

The amide linkage is one of the most important structural moieties in both chemistry and biology. Here, we briefly discuss recent advances in catalytic intermolecular C–H carbonylation reactions for the synthesis of amides, with particular attention to our intermolecular C–H amidation of arenes with carbon monoxide and organic azides to produce amides.

1 Introduction

2 Representative Methods for Amide Synthesis

3 C–H Aminocarbonylation with Carbon Monoxide and Amines

4 C–H Amidation to Amides with Carbon Monoxide and Azides

5 Summary and Outlook

Key words

C–H functionalization - amidation - carbon monoxide - azides - isocyanates - amide

Volltext

Referenzen

References

1a Ananthanarayanan VS, Tetreault S, Saint-Jean A. J. Med. Chem. 1993; 36: 1324
1b Hill DJ, Mio MJ, Prince RB, Hughes TS, Moore JS. Chem. Rev. 2001; 101: 3893
1c Valeur E, Bradley M. Chem. Soc. Rev. 2009; 38: 606

2 Graul A, Castaner J. Drugs Future 1997; 22: 956
3 Ahmed AM, Doheim MF, Mattar OM, Sherif NA, Truong DH, Le Hoa PT, Hirayama K, Huy NT. J. Med. Virol. 2017; 90: 907
4 Stilgenbauer S, Eichhorst B, Schetelig J, Hillmen P, Seymour JF, Coutre S, Jurczak W, Mulligan SP, Schuh A, Assouline S, Wendtner C.-M, Roberts AW, Davids MS, Bloehdorn J, Munir T, Böttcher S, Zhou L, Salem AH, Desai M, Chyla B, Arzt J, Kim SY, Verdugo M, Gordon G, Hallek M, Wierda WG. J. Clin. Oncol. 2018; 36: 1973

5a Amino Acids, Peptides and Proteins in Organic Chemistry. Hughes AB. Wiley; Weinheim: 2011

6a Lundberg H, Tinnis F, Selander N, Adolfsson H. Chem. Soc. Rev. 2014; 43: 2714
6b Shi S, Nolan SP, Szostak M. Acc. Chem. Res. 2018; 51: 2589
6c Liu C, Szostak M. Chem. Eur. J. 2017; 23: 7157
6d Dander JE, Garg NK. ACS Catal. 2017; 7: 1413
6e Li G, Szostak M. Nat. Commun. 2018; 9: 4165

7a Dunetz JR, Magano J, Weisenburger GA. Org. Process Res. Dev. 2016; 20: 140
7b El-Faham A, Albericio F. Chem. Rev. 2011; 111: 6557
7c Montalbetti CA. G. N, Falque V. Tetrahedron 2005; 61: 10827

8a Ishihara K. Tetrahedron 2009; 65: 1085
8b Marcelli T. Angew. Chem. Int. Ed. 2010; 49: 6840
8c Charville H, Jackson D, Hodges G, Whiting A. Chem. Commun. 2010; 46: 1813
8d Lundberg H, Tinnis F, Adolfsson H. Chem. Eur. J. 2012; 18: 3822
8e Allen CL, Chhatwal AR, Williams JM. J. Chem. Commun. 2012; 48: 666
8f Lanigan RM, Sheppard TD. Eur. J. Org. Chem. 2013; 7453
8g Morimoto H, Fujiwara R, Shimizu Y, Morisaki K, Ohshima T. Org. Lett. 2014; 16: 2018
8h Szostak R, Shi SC, Meng GR, Lalancette R, Szostak M. J. Org. Chem. 2016; 81: 8091

9a Ishihara K, Ohara S, Yamamoto H. J. Org. Chem. 1996; 61: 4196
9b Al-Zoubi RM, Marion O, Hall DG. Angew. Chem. Int. Ed. 2008; 47: 2876
9c Gernigon N, Al-Zoubi RM, Hall DG. J. Org. Chem. 2012; 77: 8386
9d Yamashita R, Sakakura A, Ishihara K. Org. Lett. 2013; 15: 3654
9e Fatemi S, Gernigon N, Hall DG. Green Chem. 2015; 17: 4016
9f Ishihara K, Lu Y. Chem. Sci. 2016; 7: 1276
9g Noda H, Furutachi M, Asada Y, Shibasaki M, Kumagai N. Nat. Chem. 2017; 9: 571
9h Wang K, Lu Y, Ishihara K. Chem. Commun. 2018; 54: 5410
9i Michigami K, Sakaguchi T, Takemoto Y. ACS Catal. 2020; 10: 683

10a Pattabiraman VR, Bode JW. Nature 2011; 480: 471
10b Allen CL, Williams JM. J. Chem. Soc. Rev. 2011; 40: 3405
10c de Figueiredo RM, Suppo J.-S, Campagne J.-M. Chem. Rev. 2016; 116: 12029
10d Sabatini MT, Boulton LT, Sneddon HF, Sheppard TD. Nat. Catal. 2019; 2: 10
10e Wang X. Nat. Catal. 2019; 2: 98

11a Bode JW, Sohn SS. J. Am. Chem. Soc. 2007; 129: 13798
11b Chiang P.-C, Kim Y, Bode JW. Chem. Commun. 2009; 4566
11c Vora HU, Rovis T. J. Am. Chem. Soc. 2007; 129: 13796
11d De Sarkar S, Studer A. Org. Lett. 2010; 12: 1992

12a Gusev DG. ACS Catal. 2017; 7: 6656
12b Chen C, Hong SH. Org. Biomol. Chem. 2011; 9: 20
12c Gunanathan C, Ben-David Y, Milstein D. Science 2007; 317: 790
12d Fujita K.-i, Takahashi Y, Owaki M, Yamamoto K, Yamaguchi R. Org. Lett. 2004; 6: 2785
12e Naota T, Murahashi S.-I. Synlett 1991; 693

13a Sabot C, Kumar KA, Mioskowski C. Tetrahedron Lett. 2007; 48: 3863
13b Yang X, Birman VB. Org. Lett. 2009; 11: 1499
13c McPherson CG, Caldwell N, Jamieson C, Simpson I, Watson AJ. B. Org. Biomol. Chem. 2017; 15: 3507
13d Lenstra DC, Nguyen DT, Mecinović J. Tetrahedron 2015; 71: 5547
13e Nguyen DT, Lenstra DC, Mecinović J. RSC Adv. 2015; 5: 77658
13f Sanz Sharley DD, Williams JM. J. Chem. Commun. 2017; 53: 2020

14a Peng J.-B, Wu F.-P, Wu X.-F. Chem. Rev. 2019; 119: 2090
14b Matsubara H, Kawamoto T, Fukuyama T, Ryu I. Acc. Chem. Res. 2018; 51: 2023
14c Li Y, Hu Y, Wu X.-F. Chem. Soc. Rev. 2018; 47: 172
14d Bai Y, Davis DC, Dai M. J. Org. Chem. 2017; 82: 2319
14e Wu X.-F, Neumann H, Beller M. Chem. Rev. 2013; 113: 1

15 Brennführer A, Neumann H, Beller M. Angew. Chem. Int. Ed. 2009; 48: 4114
16 Schoenberg A, Heck RF. J. Org. Chem. 1974; 39: 3327

17a Liu J, Li HQ, Spannenberg A, Franke R, Jackstell R, Beller M. Angew. Chem. Int. Ed. 2016; 55: 13544
17b Zhang GJi X, Yu H, Yang L, Jiao P, Huang H. Tetrahedron Lett. 2016; 57: 383
17c Dong K, Fang X, Jackstell R, Laurenczy G, Li Y, Beller M. J. Am. Chem. Soc. 2015; 137: 6053
17d Shi R, Zhang H, Lu L, Gan P, Sha Y, Zhang H, Beller M, Lei A. Chem. Commun. 2015; 51: 3247
17e Li W, Liu C, Zhang H, Ye K, Zhang G, Zhang W, Duan Z, You S, Lei A. Angew. Chem. Int. Ed. 2014; 53: 2443
17f Li W, Wu X.-F. Chem. Eur. J. 2015; 21: 7374
17g Yin Z, Wang Z, Li W, Wu X.-F. Eur. J. Org. Chem. 2017; 2017: 1769
17h Ren L, Li X, Jiao N. Org. Lett. 2016; 18: 5852
17i Li X, Li X, Jiao N. J. Am. Chem. Soc. 2015; 137: 9246
17j Zhang J, Hou Y, Ma Y, Szostak M. J. Org. Chem. 2019; 84: 338

18 Orito K, Horibata A, Nakamura T, Ushito H, Nagasaki H, Yuguchi M, Yamashita S, Tokuda M. J. Am. Chem. Soc. 2004; 126: 14342

19a Zhu C, Liu J, Li M.-B, Bäckvall JE. Chem. Soc. Rev. 2020; 49: 341
19b Liang D, Hu ZW, Peng J, Huang J, Zhu Q. Chem. Commun. 2013; 49: 173
19c Rajeshkumar V, Lee T.-H, Chuang S.-C. Org. Lett. 2013; 15: 1468
19d Taneda H, Inamoto K, Kondo Y. Org. Lett. 2016; 18: 2712
19e Zhang C, Ding Y, Gao Y, Li S, Li G. Org. Lett. 2018; 20: 2595
19f López B, Rodriguez A, Santos D, Albert J, Ariza X, Garcia J, Granell J. Chem. Commun. 2011; 47: 1054
19g Albert J, Ariza X, Calvet T, Font-Bardia M, Garcia J, Granell J, Lamela A, López B, Martinez M, Ortega L, Rodriguez A, Santos D. Organometallics 2013; 32: 649
19h McNally A, Haffemayer B, Collins BS. L, Gaunt MJ. Nature 2014; 510: 129
19i Calleja J, Pla D, Gorman TW, Domingo V, Haffemayer B, Gaunt MJ. Nat. Chem. 2015; 7: 1009
19j Willcox D, Chappell BG. N, Hogg KF, Calleja J, Smalley AP, Gaunt MJ. Science 2016; 354: 851
19k Cabrera-Pardo JR, Trowbridge A, Nappi M, Ozaki K, Gaunt MJ. Angew. Chem. Int. Ed. 2017; 56: 11958
19l Hogg KF, Trowbridge A, Alvarez-Pérez A, Gaunt MJ. Chem. Sci. 2017; 8: 8198
19m Zhang L, Wang C, Han J, Huang Z.-B, Zhao Y. J. Org. Chem. 2016; 81: 5256
19n Guo S, Wang F, Sun L, Zhang X, Fan X. Adv. Synth. Catal. 2018; 360: 2537
19o Liang D, He Y, Zhu Q. Org. Lett. 2014; 16: 2748
19p Han H, Yang S.-D, Xia J.-B. J. Org. Chem. 2019; 84: 3357
19q Ho DK. H, Calleja J, Gaunt MJ. Synlett 2019; 30: 454

20a Han H, Zhang T, Yang S.-D, Lan Y, Xia J.-B. Org. Lett. 2019; 21: 1749
20b Bai X.-F, Mu Q.-C, Xu Z, Yang K.-F, Li L, Zheng Z.-J, Xia C.-G, Xu L.-W. ACS Catal. 2019; 9: 1431

21 Zhang X, Dong S, Niu X, Li Z, Fan X, Zhang G. Org. Lett. 2016; 18: 4634

22a Guan Z.-H, Chen M, Ren Z.-H. J. Am. Chem. Soc. 2012; 134: 17490
22b Li W, Duan Z, Jiang R, Lei A. Org. Lett. 2015; 17: 1397

23 Xing Q, Shi L, Lang R, Xia C, Li F. Chem. Commun. 2012; 48: 11023
24 Xing Q, Lv H, Xia C, Li F. Chem. Commun. 2017; 53: 6914
25 Xie P, Xia C, Huang H. Org. Lett. 2013; 15: 3370
26 Li Y, Dong K, Zhu F, Wang Z, Wu X.-F. Angew. Chem. Int. Ed. 2016; 55: 7227
27 Lu L, Pei X, Mei Y, Deng Y, Zhang H, Zhang L, Lei A. Chem 2018; 4: 2861

28a Nguyen Q, Sun K, Driver TG. J. Am. Chem. Soc. 2012; 134: 7262
28b Dequirez G, Pons V, Dauban P. Angew. Chem. Int. Ed. 2012; 51: 7384
28c Olivos Suarez AI, Lyaskovskyy V, Reek JN, van der Vlugt JI, de Bruin B. Angew. Chem. Int. Ed. 2013; 52: 12510
28d Zhang Z, Huang BL, Qiao GY, Zhu L, Xiao F, Chen F, Fu B, Zhang ZH. Angew. Chem. Int. Ed. 2017; 56: 4320
28e Gu Z.-Y, Liu Y, Wang F, Bao X, Wang S.-Y, Ji S.-J. ACS Catal. 2017; 7: 3893
28f Li C, Lang K, Lu H, Hu Y, Cui X, Wojtas L, Zhang XP. Angew. Chem. Int. Ed. 2018; 57: 16837
28g Lee S, Lei H, Rovis T. J. Am. Chem. Soc. 2019; 141: 12536
28h Jung H, Keum H, Kweon J, Chang S. J. Am. Chem. Soc. 2020; 142: 5811
28i Corbin JR, Ketelboeter DR, Fernández I, Schomaker JM. J. Am. Chem. Soc. 2020; 142: 5568

29a Shimbayashi T, Sasakura K, Eguchi A, Okamoto K, Ohe K. Chem. Eur. J. 2019; 25: 3156
29b Kuijpers PF, van der Vlugt JI, Schneider S, de Bruin B. Chem. Eur. J. 2017; 23: 13819
29c Intrieri D, Zardi P, Caselli A, Gallo E. Chem. Commun. 2014; 50: 11440

30a Collman JP, Kubota M, Hosking JW. J. Am. Chem. Soc. 1967; 89: 4809
30b Bennett RP, Hardy WB. J. Am. Chem. Soc. 1968; 90: 3295
30c La Monica G, Cenini S. J. Organomet. Chem. 1981; 216: C35
30d Jenkins DM, Betley TA, Peters JC. J. Am. Chem. Soc. 2002; 124: 11238
30e Doi H, Barletta J, Suzuki M, Noyori R, Watanabe Y, Långström B. Org. Biomol. Chem. 2004; 2: 3063
30f Ren L, Jiao N. Chem. Commun. 2014; 50: 3706
30g Zhao J, Li Z, Yan S, Xu SY, Wang M.-A, Fu B, Zhang Z. Org. Lett. 2016; 18: 1736
30h Zhao J, Li Z, Song S, Wang M.-A, Fu B, Zhang Z. Angew. Chem. Int. Ed. 2016; 55: 5545
30i Feng J, Zhang Z, Li X, Zhang Z. Synlett 2020; 31: 1040

31 Yuan S.-W, Han H, Li Y.-L, Wu X, Bao X, Gu Z.-Y, Xia J.-B. Angew. Chem. Int. Ed. 2019; 58: 8887
32 Schembri LS, Eriksson J, Odell LR. J. Org. Chem. 2019; 84: 6970