Synthesis 2018; 50(16): 3187-3196
DOI: 10.1055/s-0037-1610023
special topic
© Georg Thieme Verlag Stuttgart · New York

Regio- and Stereoselective Nickel-Catalyzed Coupling of Boronic Acids with Allenoates

Yang Liu
Dipartimento di Chimica ‘G. Ciamician’–Alma Mater Studiorum, Università di Bologna, via Selmi 2, 40138 Bologna, Italy   Email: marco.bandini@unibo.it
,
Mario Daka
Dipartimento di Chimica ‘G. Ciamician’–Alma Mater Studiorum, Università di Bologna, via Selmi 2, 40138 Bologna, Italy   Email: marco.bandini@unibo.it
,
Marco Bandini*
Dipartimento di Chimica ‘G. Ciamician’–Alma Mater Studiorum, Università di Bologna, via Selmi 2, 40138 Bologna, Italy   Email: marco.bandini@unibo.it
› Author Affiliations
Acknowledgment is made to University of Bologna for financial support. Y.L. thanks Chinese Scholarship Council No. 201609120008 for funding support.
Further Information

Publication History

Received: 27 March 2018

Accepted after revision: 23 April 2018

Publication Date:
12 June 2018 (online)

Published as part of the Special Topic Modern Coupling Approaches and their Strategic Applications in Synthesis

Abstract

The Ni(II)-catalyzed cross-coupling of arylboronic acids with allenoates is documented. The high regio- and stereoselectivity of the process enables a wide range of β-aryl β,γ-unsaturated esters to be prepared in good to excellent yields (up to 95%) and high E/Z-selectivity. Additionally, [3+2]-cascade sequence was observed when 2-formylphenylboronic acid was employed.

Supporting Information

 
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