Palladium-Catalyzed C(sp²)−H Olefination/Annulation Cascades of Aryl Carboxamides Assisted by N,S-Bidentate Auxiliary

Abstract

A palladium(II)-catalyzed olefination/annulation of aryl carboxamides, assisted by an N, S-bidentate auxiliary, with methyl acrylate is described. Various carboxamides with a number of functional groups were compatible with this reaction to afford, regioselectively and in moderate yield, (E)-3-methyleneisoindolin-1-one derivatives bearing an alkyl(aryl)thio group.

Key words

palladium(II)-catalyzed - olefination - annulation - carboxamides - N,S-bidentate directing group - isoindoles

• References


For selected examples of metal-catalyzed C–H activations, see:
• 1a Daugulis O, Do H.-Q, Shabashov D. Acc. Chem. Res. 2009; 42: 1074
• 1b Xu L.-M, Li B.-J, Yang Z, Shi Z.-J. Chem. Soc. Rev. 2010; 39: 712
• 1c Sehnal P, Taylor RJ. K, Fairlamb IJ. S. Chem. Rev. 2010; 110: 824
• 1d Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
• 1e Yeung CS, Dong VM. Chem. Rev. 2011; 111: 1215
• 1f Ghorai D, Müller V, Keil H, Stalke D, Zanoni G, Tkachenko BA, Schreiner PR, Ackermann L. Adv. Synth. Catal. 2017; 359: 3137
• 1g Yang Y, Lan J, You J. Chem. Rev. 2017; 117: 8787
• 1h Labinge JA. Chem. Rev. 2017; 117: 8483
• 1i Shang R, Ilies L, Nakamura E. Chem. Rev. 2017; 117: 9086
• 1j Arockiam PB, Bruneau C, Dixneuf PH. Chem. Rev. 2012; 112: 5879
• 1k He J, Wasa M, Chan KS. L, Shao Q, Yu J.-Q. Chem. Rev. 2017; 117: 8754
• 1l Guo X.-X, Gu D.-W, Wu Z, Zhang W. Chem. Rev. 2015; 115: 1622
• 2a Shang M, Wang H.-L, Sun S-Z, Dai H.-X, Yu J.-Q. J. Am. Chem. Soc. 2014; 136: 11590
• 2b Liu Y.-J, Liu Y-H, Yan S-Y, Shi B.-F. Chem. Commun. 2015; 51: 6388
• 2c Zhao S, Liu B, Zhan B.-B, Zhang W.-D, Shi B-F. Org. Lett. 2016; 18: 4586
• 2d Hu L, Chen X, Gui Q, Tan Z, Zhu G. Chem. Commun. 2016; 52: 6845
• 2e Colby DA, Bergman RG, Ellman JA. Chem. Rev. 2010; 110: 624
• 3a Zhai S, Qiu S, Chen X, Wu J, Zhao H, Tao C, Li Y, Cheng B, Wang H, Zhai H. Chem. Commun. 2018; 54: 98
• 3b Guan M, Pang Y, Zhang J, Zhao Y. Chem. Commun. 2016; 52: 7043
• 3c Li X, Sun M, Liu K, Liu P. Adv. Synth. Catal. 2015; 357: 395
• 4a Li D.-D, Yuan T.-T, Wang G-W. Chem. Commun. 2011; 47: 12789
• 4b Wrigglesworth JW, Cox B, Lloyd-Jones GC, Booker-Milburn KI. Org. Lett. 2011; 13: 5326
• 5a Chia Y.-C, Chang F.-R, Teng C.-M, Wu Y.-C. J. Nat. Prod. 2000; 63: 1160
• 5b Couture A, Deniau E, Grandclaudon P, Rybalko-Rosen H, Leonce S, Pfeiffer B, Renard P. Bioorg. Med. Chem. Lett. 2002; 12: 3557
• 5c Lamblin M, Couture A, Deniau E, Grandclaudon P. Org. Biomol. Chem. 2007; 5: 1466
• 5d Kanamitsu N, Osaki T, Itsuji Y, Yoshimura M, Tsujimoto H, Soga M. Chem. Pharm. Bull. 2007; 55: 1682
• 5e Botero Cid HM, Trankle C, Baumann K, Pick R, Mies-Klomfass E, Kostenis E, Mohr K, Holzgrabe U. J. Med. Chem. 2000; 43: 2155
• 5f Hatoum F, Engler J, Zelmer C, Wiben J, Motti CA, Lex J, Oelgemoller M. Tetrahedron Lett. 2012; 53: 5573
• 5g Wang Z, Zhu F, Li Y, Wu X.-F. ChemCatChem 2017; 9: 94
• 5h Vijayavardhini S, Rambabu D, Anuradha V, Kapavarapu R, Rao MV. B, Pal M. Lett. Drug Des. Discovery 2014; 11: 1188
• 6 Zaitsev VG, Shabashov D, Daugulis O. J. Am. Chem. Soc. 2005; 127: 13154
• 7a Yu L, Huang H, Chen X, Hu L, Yu Y, Tan Z. Chem. Commun. 2017; 53: 4597
• 7b Zhang J, Chen H, Lin C, Liu Z, Wang C, Zhang Y. J. Am. Chem. Soc. 2015; 137: 12990
• 7c Dong J, Wang F, You J. Org. Lett. 2014; 16: 2884
• 7d Zhu W, Wang B, Zhou S, Liu H. Beilstein J. Org. Chem. 2015; 11: 1624
• 7e Liang H.-W, Ding W, Jiang K, Shuai L, Yuan Y, Wei Y, Chen Y.-C. Org. Lett. 2015; 17: 2764
• 7f Lin C, Zhang J, Chen Z, Liu Y, Liu Z, Zhang Y. Adv. Synth. Catal. 2016; 358: 1778
• 7g Zhang J, Li D, Chen H, Wang B, Liu Z, Zhang Y. Adv. Synth. Catal. 2016; 358: 792
• 7h Zhang Y, Wang Q, Yu H, Huang Y. Org. Biomol. Chem. 2014; 12: 8844
• 8a 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
• 8b 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
• 8c Hao X.-Q, Du C, Zhu X, Li P.-X, Zhang J.-H, Liu J.-H, Song M.-P. Org. Lett. 2016; 18: 3610
• 9a Noisier AF. M, Brimble MA. Chem. Rev. 2014; 114: 8775
• 9b Gopalakrishnan B, Mohan S, Parella R, Babu SA. J. Org. Chem. 2016; 81: 8988
• 9c Rouquet G, Chatani N. Angew. Chem. Int. Ed. 2013; 52: 11726
• 9d Parella R, Gopalakrishnan B, Babu SA. J. Org. Chem. 2013; 78: 11911
• 9e Gutekunst WR, Baran PS. J. Am. Chem. Soc. 2011; 133: 19076
• 9f Padmavathi R, Sankar R, Gopalakrishnan B, Parella R, Babu SA. Eur. J. Org. Chem. 2015; 3727
• 9g Tran LD, Daugulis O. Angew. Chem. Int. Ed. 2012; 51: 5188
• 9h Shabashov D, Daugulis O. J. Am. Chem. Soc. 2010; 132: 3965
• 9i Parella R, Gopalakrishnan B, Babu SA. Org. Lett. 2013; 15: 13
• 9j Zhu F, Wang Z.-X. Org. Lett. 2015; 17: 1601
• 9k Uetake Y, Niwa T, Hosoya T. Org. Lett. 2016; 18: 2758
• 10a Correa A, Carril M, Bolm C. Angew. Chem. Int. Ed. 2008; 47: 2880 ; Angew. Chem. 2008, 120, 2922
• 10b Nakamura I, Sato T, Yamamoto Y. Angew. Chem. Int. Ed. 2006; 45: 4473
• 10c Yu M, Xie Y, Xie C, Zhang Y. Org. Lett. 2012; 14: 2164
• 11a Zhang X.-S, Jiao J.-Y, Zhang X.-H, Hu B-L, Zhang X.-G. J. Org. Chem. 2016; 81: 5710
• 11b Zhang X.-S, Li G, Zhang X.-G, Zhang X.-H. Tetrahedron 2015; 71: 5458
• 11c Shi L.-F, Zhang X.-G, Zhang X.-H. Tetrahedron 2016; 72: 8617
• 11d Li X.-F, Shi L.-F, Zhang X.-G, Zhang X.-H. Org. Biomol. Chem. 2018; 16: 6438
• 12 Zhang Z, Tan J, Wang Z. Org. Lett. 2008; 10: 173