Synthesis 2020; 52(13): 1969-1980
DOI: 10.1055/s-0039-1690848
paper
© Georg Thieme Verlag Stuttgart · New York

Co(II)-Catalyzed Desilylative Annulation of Benzamides and Acrylamides with Alkynylsilanes: Access to 3-Methyleneisoindolin-1-one and 5-Methylene-1H-pyrrol-2(5H)-one Derivatives

Jingyu Wang §
,
Qiuxun Teng §
,
Cong Lin
,
Fei Gao
,
Xiuhong Liu
,
Liang Shen
Jiangxi Engineering Laboratory of Waterborne Coatings, College of Chemistry and Chemical Engineering, Jiangxi Science & Technology Normal University, Nanchang 330013, P. R. of China   Email: conglin0127@jxstnu.com.cn
› Author Affiliations
Funding from Natural Science Foundation of China (No. 51963010 and 21704036) and Science Funds of the Education Office of Jiangxi Province (No. GJJ180601) is acknowledged.
Further Information

Publication History

Received: 02 December 2019

Accepted after revision: 13 February 2020

Publication Date:
03 March 2020 (online)


§ These authors contributed equally.

Abstract

The cobalt-catalyzed desilylative annulation of C(sp2)–H bonds of benzamides and acrylamides with alkynylsilanes assisted by an 8-aminoquinolyl directing group is reported. A variety of benzamides and acrylamides were compatible in this protocol to construct various 3-methyleneisoindolin-1-one and 5-methylene-1H-pyrrol-2(5H)-one derivatives with Z-configuration selectivity in moderate to high yields.

Supporting Information

 
  • References

    • 1a Li W.-R, Lin ST, Hsu N.-M, Chern M.-S. J. Org. Chem. 2002; 67: 4702
    • 1b Bessho J.-i, Shimotsu Y, Mizumoto S, Mase N, Yoda H, Takabe K. Heterocycles 2004; 63: 1013
    • 1c Felluga F, Ghelfi F, Pagnoni UM, Parsons AF, Pattarozzi M, Roncaglia F, Valentin E. Synthesis 2007; 1882
    • 1d Nay B, Riache N, Evanno L. Nat. Prod. Rep. 2009; 26: 1044
    • 1e Miyazaki H, Miyake T, Terakawa Y, Ohmizu H, Ogiku T, Ohtani A. Bioorg. Med. Chem. Lett. 2010; 20: 546
    • 1f Anselmi E, Cherry K, Maaliki C, Inack Ngi S, Duchêne A, Thibonnet J, Abarbri M. Synthesis 2016; 48: 1407
    • 2a Flitsch W, Peters H. Tetrahedron Lett. 1969; 1161
    • 2b Rys V, Couture A, Deniau E, Grandclaudon P. Tetrahedron 2003; 59: 6615
    • 2c Kobayashi K, Matsumoto K, Nakamura D, Fukamachi S, Konishi H. Helv. Chim. Acta 2010; 93: 1048
    • 2d Reyes-González MA, Zamudio-Medina A, Ordóñez M. Tetrahedron Lett. 2012; 53: 5756
    • 3a Uozumi Y, Kawasaki N, Mori E, Mori M, Shibasaki M. J. Am. Chem. Soc. 1989; 111: 3725
    • 3b Li L, Wang M, Zhang X, Jiang Y, Ma D. Org. Lett. 2009; 11: 1309
    • 3c Kise N, Kawano Y, Sakurai T. J. Org. Chem. 2013; 78: 12453
    • 3d Chinchilla R, Nájera C. Chem. Rev. 2014; 114: 1783
    • 3e Munoz SB, Aloia AN, Moore AK, Papp A, Mathew T, Fustero S, Olah GA, Prakash GK. S. Org. Biomol. Chem. 2016; 14: 85

      For reviews, see:
    • 4a Colby DA, Bergman RG, Ellman JA. Chem. Rev. 2010; 110: 624
    • 4b Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
    • 4c Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
    • 4d Yeung CS, Dong VM. Chem. Rev. 2011; 111: 1215
    • 4e Liu C, Zhang H, Sui W, Lei A. Chem. Rev. 2011; 111: 1780
    • 4f Sun C.-L, Li B.-J, Shi Z.-J. Chem. Commun. 2010; 46: 677
    • 4g Rouquet G, Chatani N. Angew. Chem. Int. Ed. 2013; 52: 11726
    • 4h Castro LC. M, Chatani N. Chem. Lett. 2015; 44: 410
    • 4i Petrone DA, Ye J, Lautens M. Chem. Rev. 2016; 116: 8003
    • 4j Gensch T, Hopkinson MN, Glorius F, Wencel-Delord J. Chem. Soc. Rev. 2016; 45: 2900
    • 4k Kim D.-S, Park W.-J, Jun C.-H. Chem. Rev. 2017; 117: 8977
    • 4l Park Y, Kim Y, Chang S. Chem. Rev. 2017; 117: 9247
    • 4m Santhoshkumar R, Cheng C.-H. Chem. Eur. J. 2019; 25: 9366
    • 4n Rej S, Chatani N. Angew. Chem. Int. Ed. 2019; 58: 8304
    • 5a Wrigglesworth JW, Cox B, Lloyd-Jones GC, Booker-Milburn KI. Org. Lett. 2011; 13: 5326
    • 5b Patureau FW, Besset T, Glorius F. Angew. Chem. Int. Ed. 2011; 50: 1064
    • 5c Wei X, Wang F, Song G, Du Z, Li X. Org. Biomol. Chem. 2012; 10: 5521
    • 5d Zhou B, Hou W, Yang Y, Li Y. Chem. Eur. J. 2013; 19: 4701
    • 5e Cai S, Chen C, Shao P, Xi C. Org. Lett. 2014; 16: 3142
    • 5f Reddy MC, Jeganmohan M. Org. Lett. 2014; 16: 4866
    • 5g Martinez AM, Rodriguez N, Gomez Arrayas R, Carretero JC. Chem. Commun. 2014; 50: 6105
    • 5h Li XG, Sun M, Liu K, Liu PN. Adv. Synth. Catal. 2015; 357: 395
  • 6 Liang H.-W, Ding W, Jiang K, Shuai L, Yuan Y, Wei Y, Chen Y.-C. Org. Lett. 2015; 17: 2764
  • 7 Dong J, Wang F, You J. Org. Lett. 2014; 16: 2884
  • 8 Zhang Y, Wang Q, Yu H, Huang Y. Org. Biomol. Chem. 2014; 12: 8844
    • 9a Zhang L.-B, Hao X.-Q, Liu Z.-J, Zheng X.-X, Zhang S.-K, Niu J.-L, Song M.-P. Angew. Chem. Int. Ed. 2015; 54: 10012
    • 9b Hao X.-Q, Du C, Zhu X, Li P.-X, Zhang J.-H, Niu J.-L, Song M.-P. Org. Lett. 2016; 18: 3610
    • 9c Zheng X.-X, Du C, Zhao X.-M, Zhu X, Suo J.-F, Hao X.-Q, Niu J.-L, Song M.-P. J. Org. Chem. 2016; 81: 4002
    • 9d Wang Y, Du C, Wang Y, Guo X, Fang L, Song M.-P, Niu J.-L, Wei D. Adv. Synth. Catal. 2018; 360: 2668
    • 10a Zhang J, Chen H, Lin C, Liu Z, Wang C, Zhang Y. J. Am. Chem. Soc. 2015; 137: 12990
    • 10b Lin C, Zhang J, Chen Z, Liu Y, Liu Z, Zhang Y. Adv. Synth. Catal. 2016; 358: 1778
    • 10c Zhang J, Li D, Chen H, Wang B, Liu Z, Zhang Y. Adv. Synth. Catal. 2016; 358: 792

      For selected reviews, see:
    • 12a Gao K, Yoshikai N. Acc. Chem. Res. 2014; 47: 1208
    • 12b Moselage M, Li J, Ackermann L. ACS Catal. 2016; 6: 498
    • 12c Wang S, Chen S.-Y, Yu X.-Q. Chem. Commun. 2017; 53: 3165
    • 12d Yoshino T, Matsunaga S. Adv. Synth. Catal. 2017; 359: 1245
    • 12e Usman M, Ren Z.-H, Wang Y.-Y, Guan Z.-H. Synthesis 2017; 49: 1419
    • 12f Chirila PG, Whiteoak CJ. Dalton Trans. 2017; 9721
    • 12g Loup J, Dhawa U, Pesciaioli F, Wencel-Delord J, Ackermann L. Angew. Chem. Int. Ed. 2019; 58: 12803
    • 12h Xu K, Wang Z, Zhang J, Yu L, Tan J. Org. Lett. 2015; 17: 4476
    • 12i Wang H, Zhang S, Wang Z, He M, Xu K. Org. Lett. 2016; 18: 5628
    • 12j Dey A, Thrimurtulu N, Volla CM. R. Org. Lett. 2019; 21: 3871
    • 12k Zhou X.-L, Yang F, Sun H.-L, Yin Y.-N, Ye W.-T, Zhu R. J. Am. Chem. Soc. 2011; 133: 17283
    • 13a Lee P.-S, Fujita T, Yoshikai N. J. Am. Chem. Soc. 2011; 133: 17283
    • 13b Ding Z, Yoshikai N. Angew. Chem. Int. Ed. 2012; 51: 4698
    • 14a Yoshino T, Ikemoto H, Matsunaga S, Kanai M. Angew. Chem. Int. Ed. 2013; 52: 2207
    • 14b Sun B, Yoshino T, Kanai M, Matsunaga S. Angew. Chem. Int. Ed. 2015; 54: 12968
    • 16a Song W, Ackermann L. Angew. Chem. Int. Ed. 2012; 51: 8251
    • 16b Mei R, Loup J, Ackermann L. ACS Catal. 2016; 6: 793
    • 16c Mei R, Wang H, Warratz S, Macgregor SA, Ackermann L. Chem. Eur. J. 2016; 22: 6759

      For selected examples, see:
    • 17a Chen Q, Ilies L, Nakamura E. J. Am. Chem. Soc. 2011; 133: 428
    • 17b Ilies L, Chen Q, Zeng X, Nakamura E. J. Am. Chem. Soc. 2011; 133: 5221
    • 17c Tauchert ME, Incarvito CD, Rheingold AL, Bergman RG, Ellman JA. J. Am. Chem. Soc. 2012; 134: 1482
    • 17d Yu D.-G, Gensch T, de Azambuja F, Vasquez-Cespedes S, Glorius F. J. Am. Chem. Soc. 2014; 136: 17722
    • 17e Zhao D, Kim JH, Stegemann L, Strassert CA, Glorius F. Angew. Chem. Int. Ed. 2015; 54: 4508
    • 17f Park J, Chang S. Angew. Chem. Int. Ed. 2015; 54: 14103
    • 17g Gandeepan P, Rajamalli P, Cheng C.-H. Angew. Chem. Int. Ed. 2016; 55: 4308
    • 17h Martinez AM, Rodriguez N, Gomez Arrayas R, Carretero JC. Chem. Eur. J. 2017; 23: 11669
    • 17i Li X.-C, Du C, Zhang H, Niu J.-L, Song M.-P. Org. Lett. 2019; 21: 2863
    • 18a Lin C, Shen L. ChemCatChem 2019; 11: 961
    • 18b Lin C, Gao F, Shen L. Adv. Synth. Catal. 2019; 361: 3915