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Controlling cyclization pathways in palladium(ii)-catalyzed intramolecular alkene hydro-functionalization via substrate directivity

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Abstract

We report a series of palladium(II)-catalyzed, intramolecular alkene hydrofunctionalization reactions with carbon, nitrogen, and oxygen nucleophiles to form five- and six-membered carbo- and heterocycles. In these reactions, the presence of a proximal bidentate directing group controls the cyclization pathway, dictating the ring size that is generated, even in cases that are disfavored based on Baldwin's rules and in cases where there is an inherent preference for an alternative pathway. DFT studies shed light on the origins of pathway selectivity in these processes.

Graphical abstract: Controlling cyclization pathways in palladium(ii)-catalyzed intramolecular alkene hydro-functionalization via substrate directivity

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Supplementary files

Article information


Submitted
19 Jun 2020
Accepted
16 Sep 2020
First published
22 Sep 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

Controlling cyclization pathways in palladium(II)-catalyzed intramolecular alkene hydro-functionalization via substrate directivity

X. Wang, Z. Li, B. K. Mai, J. A. Gurak, J. E. Xu, V. T. Tran, H. Ni, Z. Liu, Z. Liu, K. S. Yang, R. Xiang, P. Liu and K. M. Engle, Chem. Sci., 2020, Advance Article , DOI: 10.1039/D0SC03409F

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    [Original citation] - Published by The Royal Society of Chemistry.

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