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Issue 32, 2021
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A site-selective and stereospecific cascade Suzuki–Miyaura annulation of alkyl 1,2-bisboronic esters and 2,2′-dihalo 1,1′-biaryls

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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

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Article information


Submitted
06 Feb 2021
Accepted
09 Mar 2021
First published
15 Mar 2021

This article is Open Access

Chem. Commun., 2021,57, 3909-3912
Article type
Communication

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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