Issue 25, 2019

A regioselectivity switch in Pd-catalyzed hydroallylation of alkynes

Abstract

By exploiting the reactivity of a vinyl-Pd species, we control the regioselectivity in hydroallylation of alkynes under Pd-hydride catalysis. A monophosphine ligand and carboxylic acid combination promotes 1,5-dienes through a pathway involving isomerization of alkynes to allenes. In contrast, a bisphosphine ligand and copper cocatalyst favor 1,4-dienes via a mechanism that involves transmetalation. Our study highlights how to access different isomers by diverting a common organometallic intermediate.

Graphical abstract: A regioselectivity switch in Pd-catalyzed hydroallylation of alkynes

Supplementary files

Article information

Article type
Edge Article
Submitted
28 mar. 2019
Accepted
16 may. 2019
First published
16 may. 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2019,10, 6311-6315

A regioselectivity switch in Pd-catalyzed hydroallylation of alkynes

D. Ji, Y. Hu, H. Zheng, C. Zhao, Q. Chen and Vy M. Dong, Chem. Sci., 2019, 10, 6311 DOI: 10.1039/C9SC01527B

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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