Issue 32, 2021

A site-selective and stereospecific cascade Suzuki–Miyaura annulation of alkyl 1,2-bisboronic esters and 2,2′-dihalo 1,1′-biaryls

Abstract

A cascade Suzuki–Miyaura cross-coupling giving rise to 9,10-dihydrophenanthrenes has been developed. Using biaryls with unsymmetrical substitution-pattern full site-selectivity was observed. Furthermore, this cross-coupling of an alkyl 1,2-bisboronic pinacol ester proceeds through the challenging coupling of a secondary boronate with complete stereoretention.

Graphical abstract: A site-selective and stereospecific cascade Suzuki–Miyaura annulation of alkyl 1,2-bisboronic esters and 2,2′-dihalo 1,1′-biaryls

Supplementary files

Article information

Article type
Communication
Submitted
06 Feb 2021
Accepted
09 Mar 2021
First published
15 Mar 2021
This article is Open Access
Creative Commons BY license

Chem. Commun., 2021,57, 3909-3912

A site-selective and stereospecific cascade Suzuki–Miyaura annulation of alkyl 1,2-bisboronic esters and 2,2′-dihalo 1,1′-biaryls

S. Willems, G. Toupalas, J. C. Reisenbauer and B. Morandi, Chem. Commun., 2021, 57, 3909 DOI: 10.1039/D1CC00648G

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