Intermolecular C–H Amidation of Alkenes with Carbon Monoxide and Azides via Tandem Palladium Catalysis

Zheng-Yang Gu; Yang Wu; Feng Jin; Xiaoguang Bao; Ji-Bao Xia

doi:10.1055/a-1401-4486

Synthesis, Table of Contents

Synthesis 2021; 53(18): 3361-3371
DOI: 10.1055/a-1401-4486

special topic

Bond Activation – in Honor of Prof. Shinji Murai

Intermolecular C–H Amidation of Alkenes with Carbon Monoxide and Azides via Tandem Palladium Catalysis

Authors

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), University of Chinese Academy of Sciences, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China

^bCollege of Textiles and Clothing & Key Laboratory for Advanced Technology in Environmental Protection of Jiangsu Province, Yancheng Institute of Technology, Yancheng, 224051, P. R. of China
Yang Wu‡

^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), University of Chinese Academy of Sciences, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China
Feng Jin

^cCollege of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, P. R. of China
Xiaoguang Bao∗

^cCollege of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, 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), University of Chinese Academy of Sciences, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China

Abstract

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Abstract

An atom- and step-economic intermolecular multi-component palladium-catalyzed C–H amidation of alkenes with carbon monoxide and organic azides has been developed for the synthesis of alkenyl amides. The reaction proceeds efficiently without an ortho-directing group on the alkene substrates. Nontoxic dinitrogen is generated as the sole by-product. Computational studies and control experiments have revealed that the reaction takes place via an unexpected mechanism by tandem palladium catalysis.

Key words

C–H carbonylation - amidation - palladium - alkene - amides

Full Text

References

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 Allen CL, Williams JM. J. Chem. Soc. Rev. 2011; 40: 3405
1d Pattabiraman VR, Bode JW. Nature 2011; 480: 471
1e Lundberg H, Tinnis F, Selander N, Adolfsson H. Chem. Soc. Rev. 2014; 43: 2714
1f de Figueiredo RM, Suppo JS, Campagne JM. Chem. Rev. 2016; 116: 12029
1g Wang X. Nat. Catal. 2019; 2: 98

2a Orjala J, Gerwick WH. J. Nat. Prod. 1996; 59: 427
2b Hosoya T, Kato Y, Yamamoto Y, Hayashi M, Komiyama K, Ishibashi M. Heterocycles 2006; 69: 463
2c Wang H.-Y, Wang R.-X, Zhao Y.-X, Liu K, Wang F.-L, Sun J.-Y. Chem. Biodivers. 2015; 12: 1256
2d Yuan Y.-H, Han X, Zhu F.-P, Tian J.-M, Zhang F.-M, Zhang X.-M, Tu Y.-Q, Wang S.-H, Guo X. Nat. Commun. 2019; 10: 3394

3a Dander JE, Garg NK. ACS Catal. 2017; 7: 1413
3b Liu C, Szostak M. Chem. Eur. J. 2017; 23: 7157
3c Liu H, Song S, Wang C.-Q, Feng C, Loh T.-P. ChemSusChem 2017; 10: 58
3d Shi S, Nolan SP, Szostak M. Acc. Chem. Res. 2018; 51: 2589
3e Li G, Szostak M. Chem. Rec. 2020; 20: 649

4a Montalbetti CA. G. N, Falque V. Tetrahedron 2005; 61: 10827
4b Valeur E, Bradley M. Chem. Soc. Rev. 2009; 38: 606
4c El-Faham A, Albericio F. Chem. Rev. 2011; 111: 6557
4d Dunetz JR, Magano J, Weisenburger GA. Org. Process Res. Dev. 2016; 20: 140
4e Li G, Ma S, Szostak M. Trends Chem. 2020; 2: 914

5 Constable DJ. C, Dunn PJ, Hayler JD, Humphrey GR, Leazer JJ. L, Linderman RJ, Lorenz K, Manley J, Pearlman BA, Wells A, Zaks A, Zhang TY. Green Chem. 2007; 9: 411

6a Ishihara K, Ohara S, Yamamoto H. J. Org. Chem. 1996; 61: 4196
6b Al-Zoubi RM, Marion O, Hall DG. Angew. Chem. Int. Ed. 2008; 47: 2876
6c Ishihara K, Lu Y. Chem. Sci. 2016; 7: 1276
6d Noda H, Furutachi M, Asada Y, Shibasaki M, Kumagai N. Nat. Chem. 2017; 9: 571
6e Wang K, Lu Y, Ishihara K. Chem. Commun. 2018; 54: 5410

7a Imada Y, Alper H. J. Org. Chem. 1996; 61: 6766
7b Imada Y, Vasapollo G, Alper H. J. Org. Chem. 1996; 61: 7982
7c Uenoyama Y, Fukuyama T, Nobuta O, Matsubara H, Ryu I. Angew. Chem. Int. Ed. 2005; 44: 1075
7d Li Y, Alper H, Yu Z. Org. Lett. 2006; 8: 5199
7e Driller KM, Prateeptongkum S, Jackstell R, Beller M. Angew. Chem. Int. Ed. 2011; 50: 537
7f Gao B, Huang H. Org. Lett. 2017; 19: 6260
7g Sha F, Alper H. ACS Catal. 2017; 7: 2220

8a Modern Carbonylation Methods . Kollar L. Wiley-VCH; Weinheim: 2008
8b Transition Metal Catalyzed Carbonylation Reactions: Carbonylative Activation of C–X Bonds. Beller M, Wu X.-F. Springer; Amsterdam: 2013

9a Schoenberg A, Heck RF. J. Org. Chem. 1974; 39: 5
9b Eriksson J, Aaberg O, Laangstroem B. Eur. J. Org. Chem. 2007; 455
9c Lagerlund O, Mantel ML. H, Larhed M. Tetrahedron 2009; 65: 7646
9d Chen B, Wu X.-F. J. Catal. 2020; 383: 160

10a Ferguson J, Zeng F, Alwis N, Alper H. Org. Lett. 2013; 15: 1998
10b Grigorjeva L, Daugulis O. Org. Lett. 2014; 16: 4688
10c 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
10d Calleja J, Pla D, Gorman TW, Domingo V, Haffemayer B, Gaunt MJ. Nat. Chem. 2015; 7: 1009
10e Wang C, Zhang L, Chen C, Han J, Yao Y, Zhao Y. Chem. Sci. 2015; 6: 4610
10f Zhu J, Gao B, Huang H. Org. Biomol. Chem. 2017; 15: 2910
10g Liu S, Wang H, Dai X, Shi F. Green Chem. 2018; 20: 3457
10h Zeng L, Li H, Tang S, Gao X, Deng Y, Zhang G, Pao C.-W, Chen J.-L, Lee J.-F, Lei A. ACS Catal. 2018; 8: 5448

11a Fang X, Jackstell R, Beller M. Angew. Chem. Int. Ed. 2013; 52: 14089
11b Liu H, Yan N, Dyson PJ. Chem. Commun. 2014; 50: 7848
11c Liu J, Li H, Spannenberg A, Franke R, Jackstell R, Beller M. Angew. Chem. Int. Ed. 2016; 55: 13544
11d Zhou X, Zhang G, Gao B, Huang H. Org. Lett. 2018; 20: 2208

12a Shi R, Zhang H, Lu L, Gan P, Sha Y, Zhang H, Liu Q, Beller M, Lei A. Chem. Commun. 2015; 51: 3247
12b Peng J.-B, Geng H.-Q, Li D, Qi X, Ying J, Wu X.-F. Org. Lett. 2018; 20: 4988

13a Shen M, Lesli BE, Driver TG. Angew. Chem. Int. Ed. 2008; 47: 5056
13b Dequirez G, Pons V, Dauban P. Angew. Chem. Int. Ed. 2012; 51: 7384
13c Nguyen Q, Sun K, Driver TG. J. Am. Chem. Soc. 2012; 134: 7262
13d Olivos Suarez AI, Lyaskovskyy V, Reek JN, van der Vlugt JI, de Bruin B. Angew. Chem. Int. Ed. 2013; 52: 12510
13e Intrieri D, Zardi P, Caselli A, Gallo E. Chem. Commun. 2014; 50: 11440
13f Lu H, Li C, Jiang H, Lizardi CL, Zhang XP. Angew. Chem. Int. Ed. 2014; 53: 7028
13g Goswami M, Lyaskovskyy V, Domingos SR, Buma WJ, Woutersen S, Troeppner O, Ivanovic-Burmazovic I, Lu H, Cui X, Zhang XP, Reijerse EJ, DeBeer S, van Schooneveld MM, Pfaff FF, Ray K, de Bruin B. J. Am. Chem. Soc. 2015; 137: 5468
13h Kuijpers PF, van der Vlugt JI, Schneider S, de Bruin B. Chem. Eur. J. 2017; 23: 13819
13i Li C, Lang K, Lu H, Hu Y, Cui X, Wojtas L, Zhang XP. Angew. Chem. Int. Ed. 2018; 57: 16837
13j Shimbayashi T, Sasakura K, Eguchi A, Okamoto K, Ohe K. Chem. Eur. J. 2019; 25: 3156

14a Gu Z.-Y, Li J.-H, Wang S.-Y, Ji S.-J. Chem. Commun. 2017; 53: 11173
14b Gu Z.-Y, Liu Y, Wang F, Bao X, Wang S.-Y, Ji S.-J. ACS Catal. 2017; 7: 3893
14c Zhang Z, Huang B, Qiao G, Zhu L, Xiao F, Chen F, Fu B, Zhang Z. Angew. Chem. Int. Ed. 2017; 56: 4320
14d Gu Z.-Y, Zhang R, Wang S.-Y, Ji S.-J. Chin. J. Chem. 2018; 36: 1011
14e Lang K, Torker S, Wojtas L, Zhang XP. J. Am. Chem. Soc. 2019; 141: 12388

15a Bennett RP, Hardy WB. J. Am. Chem. Soc. 1968; 90: 3295
15b La Monica G, Cenini S. J. Organomet. Chem. 1981; 216: C35
15c Ren L, Jiao N. Chem. Commun. 2014; 50: 3706
15d Zhang Z, Xiao F, Huang B, Hu J, Fu B, Zhang Z. Org. Lett. 2016; 18: 908
15e Zhao J, Li Z, Song S, Wang M.-A, Fu B, Zhang Z. Angew. Chem. Int. Ed. 2016; 55: 5545
15f Zhao J, Li Z, Yan S, Xu S, Wang MA, Fu B, Zhang Z. Org. Lett. 2016; 18: 1736
15g Chow SY, Odell LR. J. Org. Chem. 2017; 82: 2515
15h Li Z, Xu S, Huang B, Yuan C, Chang W, Fu B, Jiao L, Wang P, Zhang Z. J. Org. Chem. 2019; 84: 9497
15i Schembri LS, Eriksson J, Odell LR. J. Org. Chem. 2019; 84: 6970
15j Feng J, Zhang Z, Li X, Zhang Z. Synlett 2020; 31: 1040
15k Zhang Y, Yin Z, Wu X.-F. Org. Lett. 2019; 21: 3242
15l Chen B, Wu X.-F. J. Catal. 2020; 383: 160
15m Yuan Y, Chen B, Zhang Y, Wu X.-F. J. Org. Chem. 2020; 85: 5733

16a 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
16b Li Y.-L, Gu Z.-Y, Xia J.-B. Synlett 2021; 32: 7

17 McGrath NA, Brichacek M, Njardarson JT. J. Chem. Educ. 2010; 87: 1348

18a D’Auria M, Racioppi R, Viggiani L, Zanirato P. Eur. J. Org. Chem. 2009; 932
18b Ferrini S, Cini E, Taddei M. Synlett 2013; 24: 491

19a Sundberg RJ. Indoles . Academic Press; San Diego: 1996
19b Inman M, Moody CJ. Chem. Sci. 2013; 4: 29
19c Patil SA, Patil R, Miller DD. Curr. Med. Chem. 2011; 18: 615

20 Kulkarni JS, Metha AA, Santani DD, Goyal RK. Pharm. Res. 2002; 46: 101

21a Effenberger F, Gleiter R. Chem. Ber. 1964; 97: 1576
21b Chmielewski M, Kaluza Z. J. Org. Chem. 1986; 51: 2395
21c Cossio FP, Roa G, Lecea B, Ugalde JM. J. Am. Chem. Soc. 1995; 117: 12306
21d Chmielewski M, Kałuża Z, Furman B. Chem. Commun. 1996; 2689

22 The transition state leading to the formation of β-lactam intermediate is located as TS3c′, which is much higher in energy than the pathway via TS3a′ (Figure 1).
23 After the formation of the isocyanate intermediate, a possible Pd(II)-catalyzed pathway to afford the final product is also considered (Figure S2 in Supporting Information). The main mechanistic difference for Pd(II)-catalyzed pathway is that the acetate ligand could serve as a proton shuttle to assist the H-migration to yield the final product.

Supplementary Material

Supporting Information (PDF)