Copper(II)-catalyzed carbon-carbon triple bond cleavage of internal alkynes for the synthesis of annulated indolizines

Jinwei Sun; Fuyao Wang; Huayou Hu; Xiangshan Wang; Hui Wu; Yun Liu

doi:10.1021/jo500456d

Copper(II)-catalyzed carbon-carbon triple bond cleavage of internal alkynes for the synthesis of annulated indolizines

J Org Chem. 2014 May 2;79(9):3992-8. doi: 10.1021/jo500456d. Epub 2014 Apr 21.

Authors

Jinwei Sun¹, Fuyao Wang, Huayou Hu, Xiangshan Wang, Hui Wu, Yun Liu

Affiliation

¹ Jiangsu Key Laboratory of Green Synthetic for Functional Materials and School of Chemistry and Chemical Engineering, Jiangsu Normal University , Xuzhou 221116, Jiangsu, PR China.

PMID: 24712380
DOI: 10.1021/jo500456d

Abstract

Cleavage of C≡C bond in butynedioates via copper(II)-catalyzed reaction has been achieved, leading to the synthesis of benzo[f]pyrido[1,2-a]indole-6,11-diones in high yields by one-pot three-component reactions. In this unprecedented C≡C bond cleavage reaction of internal alkynes, both fragments from the alkyne are successively incorporated into the products.