Pd-Catalyzed Highly Regio- and Stereoselective Formation of C-C Double Bonds: An Efficient Method for the Synthesis of Benzofuran-, Dihydrobenzofuran-, and Indoline-Containing Alkenes

Yang Gao; Wenfang Xiong; Huoji Chen; Wanqing Wu; Jianwen Peng; Yinglan Gao; Huanfeng Jiang

doi:10.1021/acs.joc.5b01024

Pd-Catalyzed Highly Regio- and Stereoselective Formation of C-C Double Bonds: An Efficient Method for the Synthesis of Benzofuran-, Dihydrobenzofuran-, and Indoline-Containing Alkenes

J Org Chem. 2015 Aug 7;80(15):7456-67. doi: 10.1021/acs.joc.5b01024. Epub 2015 Jul 20.

Authors

Yang Gao¹, Wenfang Xiong¹, Huoji Chen¹, Wanqing Wu¹, Jianwen Peng¹, Yinglan Gao¹, Huanfeng Jiang¹

Affiliation

¹ School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China.

PMID: 26158340
DOI: 10.1021/acs.joc.5b01024

Abstract

A highly regio- and stereoselective C-C double bond formation reaction via Pd-catalyzed Heck-type cascade process with N-tosylhydrazones has been developed. Various N-tosylhydrazones derived from both ketones and aldehydes are found to be efficient substrates to provide di- and trisubstituted olefins with high regio- and stereoselectivity. Furthermore, this reaction has a good functional group tolerance and different benzofuran-, dihydrobenzofuran-, and indoline-containing alkene products were obtained with high selectivity.