Issue 41, 2020

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
19 Jūn. 2020
Accepted
16 Sept. 2020
First published
22 Sept. 2020
This article is Open Access

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

Chem. Sci., 2020,11, 11307-11314

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, 11, 11307 DOI: 10.1039/D0SC03409F

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