Issue 41, 2020
From the journal:

Chemical Science

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

Xin Wang,‡ab   Zi-Qi Li,‡a   Binh Khanh Mai, ORCID logo ‡c   John A. Gurak, Jr,a   Jessica E. Xu,a   Van T. Tran,a   Hui-Qi Ni,a   Zhen Liu,a   Zhonglin Liu,a   Kin S. Yang,a   Rong Xiang,b   Peng Liu ORCID logo *c  and  Keary M. Engle ORCID logo *a  

* Corresponding authors

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

b Department of Medicinal Chemistry, School of Medicine, Nankai University, 94 Weijin Road, Tianjin 300071, China

c Department of Chemistry, University of Pittsburg, Pittsburgh, Pennsylvania 15260, USA
E-mail: pengliu@pitt.edu

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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Article information

DOI
https://doi.org/10.1039/D0SC03409F
Article type
Edge Article
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
Creative Commons BY-NC license

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

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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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