ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Regio- and stereoselective intramolecular hydroalkoxylation of aromatic alkynols: an access to dihydroisobenzofurans under transition-metal-free conditions

Shu-Yan Yu, Li-Hong Gao, Jing-Xin Wu, Hong-Bing Lan, Yi Ma, and Zhi-Gang Yin

Material and Chemical Engineering College, Zhengzhou University of Light Industry, Zhengzhou, People’s Republic of China

E-mail: yushuyan_zzuli@163.com

Received: 10 February 2020  Accepted: 4 April 2020

Abstract:

An efficient, transition-metal-free method to synthesize dihydroisobenzofuran derivatives via intramolecular hydroalkoxylation of aromatic alkynols with the promotion of cesium carbonate has been developed. The reaction proceeds regioselectively with exclusive formation of 5-exo-dig product, and only Z-isomer of the new generated double bond is observed. This new protocol features with milder reaction conditions, more convenient operation and satisfactory selectivities.

Keywords: Cesium carbonate; Intramolecular hydroalkoxylation; Dihydroisobenzofurans; Transition-metal-free

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-020-01159-5

Chemical Papers 74 (10) 3303–3310 (2020)