Palladium(II)-catalyzed γ-selective hydroarylation of alkenyl carbonyl compounds with arylboronic acids

Rei Matsuura; Tanner C. Jankins; David E. Hill; Kin S. Yang; Gary M. Gallego; Shouliang Yang; Mingying He; Fen Wang; Rohan P. Marsters; Indrawan McAlpine; Keary M. Engle

doi:10.1039/C8SC03081B

Palladium(ii)-catalyzed γ-selective hydroarylation of alkenyl carbonyl compounds with arylboronic acids†

Rei Matsuura,^a Tanner C. Jankins,^a David E. Hill,^a Kin S. Yang,^a Gary M. Gallego,^b Shouliang Yang,^b Mingying He,^b Fen Wang,^b Rohan P. Marsters,^a Indrawan McAlpine^b and Keary M. Engle

*^a

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^a Department of Chemistry, The Scripps Research Institute, 10550 N Torrey Pines Road, La Jolla, California 92037, USA
E-mail: keary@scripps.edu

^b Pfizer Oncology Medicinal Chemistry, 10770 Science Center Drive, San Diego, California 92121, USA

Abstract

A catalytic γ-selective syn-hydroarylation of alkenyl carbonyl compounds using arylboronic acids has been developed using a substrate directivity approach with a palladium(II) catalyst. This method tolerates a wide range of functionalized (hetero)arylboronic acids and a variety of substitution patterns on the alkene. Preliminary mechanistic studies suggest that transmetalation is rate-limiting.

This article is part of the themed collections: The ChemRxiv Collection and 2018 Chemical Science HOT Article Collection

Chemical Science

Palladium(ii)-catalyzed γ-selective hydroarylation of alkenyl carbonyl compounds with arylboronic acids†

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