A one-pot tandem chemoselective allylation/cross-coupling via temperature control of a multi-nucleophile/electrophile system

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Xu, Chao and Fyfe, James W.B. and Seath, Ciaran P. and Bennett, Steven H. and Watson, Allan J.B. (2017) A one-pot tandem chemoselective allylation/cross-coupling via temperature control of a multi-nucleophile/electrophile system. Chemical Communications (London), 53. pp. 9139-9142. ISSN 0009-241X (https://doi.org/10.1039/C7CC05416E)

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Abstract

A chemoselective tandem reaction of a multi-reactive, two electrophile + two nucleophile, system is reported. An allylation/cross-coupling process of a haloaryl aldehyde, an aryl BPin, and an allyl BPin can be controlled using a temperature gradient to overcome natural reactivity profiles and allow two sequential chemoselective C–C bond formations without intervention. This process offers efficient access to an array of functionalised products including pharmaceutical and natural product scaffolds.

ORCID iDs

Xu, Chao, Fyfe, James W.B. ORCID logoORCID: https://orcid.org/0000-0001-8501-9197, Seath, Ciaran P. ORCID logoORCID: https://orcid.org/0000-0002-6774-128X, Bennett, Steven H. and Watson, Allan J.B.;
CORE (COnnecting REpositories)