Issue 46, 2017

Efficient cross-coupling of aryl/alkenyl triflates with acyclic secondary alkylboronic acids

Abstract

Aryl–secondary alkyl cross-coupling with aryl sulfonate esters as coupling partners remains a significant challenge. Efficient cross-coupling between aryl/alkenyl triflates and acyclic secondary alkylboronic acids is realized for the first time to provide a series of sterically congested acyclic secondary alkyl arenes/olefins in good to excellent yields. The employment of sterically bulky P,P[double bond, length as m-dash]O ligand L1/L2 is crucial for the high yields and selectivities. The method has enabled a concise and 4-step synthesis of a key intermediate of male contraceptive agent and PAF antagonist gossypol.

Graphical abstract: Efficient cross-coupling of aryl/alkenyl triflates with acyclic secondary alkylboronic acids

Supplementary files

Article information

Article type
Paper
Submitted
12 Oct 2017
Accepted
10 Nov 2017
First published
13 Nov 2017

Org. Biomol. Chem., 2017,15, 9903-9909

Efficient cross-coupling of aryl/alkenyl triflates with acyclic secondary alkylboronic acids

T. Si, B. Li, W. Xiong, B. Xu and W. Tang, Org. Biomol. Chem., 2017, 15, 9903 DOI: 10.1039/C7OB02531A

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