Issue 7, 2015

Pd-catalyzed Heck cyclization and in situ hydrocarboxylation or hydromethenylation via a hydrogen borrowing strategy

Abstract

A Pd-catalyzed hydrocarboxylation of the in situ formed neopentylic alkenes by the use of “borrowed hydrogen” from Heck-type β-hydride elimination was reported. The advantage of this strategy is that no additional hydrogen sources or organometallic reagents were required. It was found that CHCl3 was not only used as a safe and convenient “CO” source but also proved superior in the linear/branched selectivity over carbon monoxide. Furthermore, the in situ formed neopentylic alkenes could be chemoselectively functionalized with other C–C unsaturated bonds being unchanged, even the less sterically hindered ones.

Graphical abstract: Pd-catalyzed Heck cyclization and in situ hydrocarboxylation or hydromethenylation via a hydrogen borrowing strategy

Supplementary files

Article information

Article type
Research Article
Submitted
20 mar 2015
Accepted
26 apr 2015
First published
28 apr 2015

Org. Chem. Front., 2015,2, 778-782

Pd-catalyzed Heck cyclization and in situ hydrocarboxylation or hydromethenylation via a hydrogen borrowing strategy

X. Liu and Z. Gu, Org. Chem. Front., 2015, 2, 778 DOI: 10.1039/C5QO00091B

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