Palladium-Catalyzed Carbonylation of Azides and Mechanistic Studies

Jiyao Feng; Zhen Zhang; Xuefeng Li; Zhenhua Zhang

doi:10.1055/s-0039-1690859

Synlett, Table of Contents

Synlett 2020; 31(11): 1040-1049
DOI: 10.1055/s-0039-1690859

account

Palladium-Catalyzed Carbonylation of Azides and Mechanistic Studies

Jiyao Feng

^aBeijing Advanced Innovation Center for Food Nutrition and Human Health, College of Plant Protection, and College of Science, China Agricultural University, Beijing 100193, P. R. of China

,

Zhen Zhang

^bCollege of Chemistry & Chemical Engineering, Yantai University, Yantai, 264005, P. R. of China Email: 91030@cau.edu.cn Email: zhangzhh@cau.edu.cn

,

Xuefeng Li∗

^aBeijing Advanced Innovation Center for Food Nutrition and Human Health, College of Plant Protection, and College of Science, China Agricultural University, Beijing 100193, P. R. of China

,

Zhenhua Zhang∗

^aBeijing Advanced Innovation Center for Food Nutrition and Human Health, College of Plant Protection, and College of Science, China Agricultural University, Beijing 100193, P. R. of China

› Author Affiliations

Abstract

All articles of this category

Abstract

Isocyanates are widely applied in the fields of materials science, drug discovery and chemical industry processes. Palladium-catalyzed carbonylation of azides with carbon monoxide (CO) is reported as a powerful method for simple and efficient access to isocyanates, which are important precursors for preparing structurally meaningful urea, carbamate and amidine derivatives. In this account, we provide an overview on the synthesis of isocyanates and their subsequent reactions to obtain diverse nucleophilic addition products. In addition, with particular emphasis on our mechanistic studies of the Pd-catalyzed carbonylation process, we outline the identification of the actual catalytic species, the possible intermediates and some key factors in the catalytic cycle.

1 Introduction

2 Palladium-Catalyzed Reaction of Azides with CO and Subsequent Nucleophilic Additions

3 Mechanistic Studies on the Palladium-Catalyzed Reaction of Azides with CO

3.1 Studies on the Actual Catalytic Species and the Key Intermediates in the Activation and Carbonylation of Acyl Azides

3.2 Study of the Sulfonylurea Product Self-Catalyzed Carbonylation of Sulfonyl Azides

3.3 Study of the Actual Catalytic Pattern of the Pd/C Catalyst

4 Conclusion

Key words

azides - isocyanates - palladium catalysts - carbon monoxide - ureas

Full Text

References

References

1a Braunstein P, Nobel D. Chem. Rev. 1989; 89: 1927
1b Rigby JH. Synlett 2000; 1
1c Varela JA, Saa C. Chem. Rev. 2003; 103: 3787
1d Allen AD, Tidwell TT. Chem. Rev. 2013; 113: 7287
1e Delebecq E, Pascault JP, Boutevin B, Ganachaud F. Chem. Rev. 2013; 113: 80

2a Slocombe RJ, Hardy EE, Saunders JH, Jenkins RL. J. Am. Chem. Soc. 1950; 72: 1888
2b Eckert H, Forster B. Angew. Chem. Int. Ed. 1987; 26: 894

3 Shi F. J. Catal. 2003; 219: 372
4 Buchner E, Curtius T. Chem. Ber. 1885; 18: 2371
5 Hofmann AW. Ber. Dtsch. Chem. Ges. 1881; 14: 2725
6 Lossen W. Liebigs Ann. Chem. 1869; 150: 313
7 Collman JP, Kubota M, Hosking JW. J. Am. Chem. Soc. 1967; 89: 4809
8 Bennett RP, Hardy WB. J. Am. Chem. Soc. 1968; 90: 3295

9a Doi H, Barletta J, Suzuki M, Noyori R, Watanabe Y, Langstrom B. Org. Biomol. Chem. 2004; 2: 3063
9b Åberg O, Långström B. J. Comb. Chem. 2011; 54: 38

10a Handbook of Organopalladium Chemistry for Organic Synthesis. Negishi E. John Wiley & Sons; New York: 2002
10b Tsuji J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century. John Wiley & Sons; Chichester: 2004
10c Xiao Q, Zhang Y, Wang J. Acc. Chem. Res. 2013; 46: 236
10d Wu X.-F, Neumann H, Beller M. Chem. Soc. Rev. 2011; 40: 4986

11a Zhang Z, Liu Y, Gong M, Zhao X, Zhang Y, Wang J. Angew. Chem. Int. Ed. 2010; 49: 1139
11b Zhou P.-X, Zhou Z.-Z, Chen Z.-S, Ye Y.-Y, Zhao L.-B, Yang Y.-F, Xia X.-F, Luo J.-Y, Liang Y.-M. Chem. Commun. 2013; 49: 561
11c Liu Y, Zhang Z, Zhang S, Zhang Y, Wang J, Zhang Z. Chem. Asian J. 2018; 13: 3658

12a Zhang Z, Liu Y, Ling L, Li Y, Dong Y, Gong M, Zhao X, Zhang Y, Wang J. J. Am. Chem. Soc. 2011; 133: 4330
12b Zhang Z, Zhang Y, Wang J. ACS Catal. 2011; 1: 1621

13 Miloserdov FM, Grushin VV. Angew. Chem. Int. Ed. 2012; 51: 3668
14 Ren L, Jiao N. Chem. Commun. 2014; 50: 3706
15 Izzo AA, Ernst E. Drugs 2009; 69: 1777
16 Lentza-Rizos C, Balokas A. J. Agric. Food Chem. 2001; 49: 710
17 Zhao J, Li Z, Song S, Wang MA, Fu B, Zhang Z. Angew. Chem. Int. Ed. 2016; 55: 5545
18 Li Z, Xu S, Huang B, Yuan C, Chang W, Fu B, Jiao L, Wang P, Zhang Z. J. Org. Chem. 2019; 84: 9497
19 Zhao J, Li Z, Yan S, Xu S, Wang MA, Fu B, Zhang Z. Org. Lett. 2016; 18: 1736

20a Zhang CL, Katoh M, Shibasaki T, Minami K, Sunaga Y, Takahashi H, Yokoi N, Iwasaki M, Miki T, Seino S. Science 2009; 325: 607
20b Guan A, Liu C, Yang X, Dekeyser M. Chem. Rev. 2014; 114: 7079

21a Chow SY, Stevens MY, Odell LR. J. Org. Chem. 2016; 81: 2681
21b Chow SY, Odell LR. J. Org. Chem. 2017; 82: 2515
21c Schembri LS, Eriksson J, Odell LR. J. Org. Chem. 2019; 84: 6970
21d Mozaffari M, Nowrouzi N. Eur. J. Org. Chem. 2019; 46: 7541

22 Chen B, Peng JB, Ying J, Qi X, Wu X.-F. Adv. Synth. Catal. 2018; 360: 4585
23 Wang L, Wang H, Li G, Min S, Xiang F, Liu S, Zheng W. Adv. Synth. Catal. 2018; 360: 2820
24 Karmouta MG, Miocque M, Derdour A, Gayral P, Lafont O. Eur. J. Med. Chem. 1989; 24: 547
25 Willcox D, Chappell BG, Hogg KF, Calleja J, Smalley AP, Gaunt MJ. Science 2016; 354: 851

26a Mindiola DJ, Hillhouse GL. J. Am. Chem. Soc. 2001; 123: 4623
26b Jenkins DM, Betley TA, Peters JC. J. Am. Chem. Soc. 2002; 124: 11238
26c Scepaniak JJ, Bontchev RP, Johnson DL, Smith JM. Angew. Chem. Int. Ed. 2011; 50: 6630

27a Badiei YM, Krishnaswamy A, Melzer MM, Warren TH. J. Am. Chem. Soc. 2006; 128: 15056
27b Laskowski CA, Hillhouse GL. Organometallics 2009; 28: 6114

28 Cenini S, Gallo E, Caselli A, Ragaini F, Fantauzzi S, Piangiolino C. Coord. Chem. Rev. 2006; 250: 1234

29a Besenyei G, Párkányi L, Foch L, Simándi LI, Kálmán A. Chem. Commun. 1997; 12: 1143
29b Besenyei G, Párkányi L, Szalontai G, Holly S, Pápai I, Keresztury G, Nagy A. Dalton Trans 2004; 13: 2041

30 All calculations were performed using the Gaussian 09 program. The density functional theory (DFT) formalism with the B3LYP functional and LanL2DZ mixed basis sets for Pd atoms and the 6-31G(d,p) basis sets for other main group atoms were applied. Thermodynamic parameters including the Gibbs free energies at 298 K were obtained by frequency calculations. Transition states are realized by the presence of a single negative frequency. The electronic energies of the optimized structures were further corrected by single-point calculations of the M06-D3 functionals with SDD for Pd atoms and 6-311+G(d,p) for other atoms. Single-point solvation energy corrections in THF computed by the ief-PCM method were added to the gas-phase free energy.
31 Heidenreich RG, Krauter JG. E, Pietsch J, Köhler K. J. Mol. Catal. A: Chem. 2002; 182–183: 499