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

doi:10.1055/s-0039-1690848

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(13): 1969-1980
DOI: 10.1055/s-0039-1690848

paper

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

Authors

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

Abstract

Alle Artikel dieser Rubrik

^§ 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.

Key words

cobalt catalysis - desilylative annulation - benzamides and acrylamides - alkynylsilanes - 3-methyleneisoindolin-1-one - 5-methylene-1H-pyrrol-2(5H)-one

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Referenzen

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

11a Larson GL. Synthesis 2018; 50: 2433
11b Lin C, Shen L. RSC Adv. 2019; 9: 30650

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

15a Grigorjeva L, Daugulis O. Angew. Chem. Int. Ed. 2014; 53: 10209
15b Grigorjeva L, Daugulis O. Org. Lett. 2014; 16: 4684
15c Grigorjeva L, Daugulis O. Org. Lett. 2014; 16: 4688
15d Grigorjeva L, Daugulis O. Org. Lett. 2015; 17: 1204

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

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