Directed Remote Lateral Metalation: Highly Substituted 2-Naphthols and BINOLs by in situ Directing Group Generation

Snieckus, Victor; Kitching, Matthew; Laars, Marju; Board, Johnathan; Patel, Jignesh; Gan, Wei

doi:10.1002/ange.201805203

Directed Remote Lateral Metalation: Highly Substituted 2-Naphthols and BINOLs by in situ Directing Group Generation

Snieckus, Victor; Kitching, Matthew; Laars, Marju; Board, Johnathan; Patel, Jignesh; Gan, Wei

Authors

Victor Snieckus

Dr Matthew Kitching matthew.o.kitching@durham.ac.uk
Royal Society University Research Fellow

Marju Laars

Johnathan Board

Jignesh Patel

Wei Gan

Abstract

A general synthesis of highly substituted 2‐naphthols based on a new carbanionic reaction sequence is demonstrated. The reaction exploits the dual nature of lithium bases consisting of consecutive ring opening of readily available coumarins with LiNEt2 or LDA to Z‐cinnamamides generating a directing group in situ and allowing, by conformational freedom, a lateral directed remote metalation ‐ ring closure reaction to give the aryl 2‐naphthols in good to excellent yields. These transformations can be combined to provide a more efficient one pot process. Mechanistic insight into the remote lateral metalation step demonstrating the requirement of Z‐cinnamamide is described. Application of this methodology to the synthesis of highly substituted 3,3'‐diaryl BINOL ligands is also reported.

Citation

Snieckus, V., Kitching, M., Laars, M., Board, J., Patel, J., & Gan, W. (2018). Directed Remote Lateral Metalation: Highly Substituted 2-Naphthols and BINOLs by in situ Directing Group Generation. Angewandte Chemie, 130(30), 9569-9573. https://doi.org/10.1002/ange.201805203

Journal Article Type	Article
Acceptance Date	May 30, 2018
Online Publication Date	Jun 21, 2018
Publication Date	Jul 20, 2018
Deposit Date	Jun 4, 2018
Publicly Available Date	Jun 4, 2018
Journal	Angewandte Chemie
Print ISSN	0044-8249
Electronic ISSN	1521-3757
Publisher	Wiley
Peer Reviewed	Peer Reviewed
Volume	130
Issue	30
Pages	9569-9573
DOI	https://doi.org/10.1002/ange.201805203

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Copyright Statement
This is the peer reviewed version of the following article: Snieckus, Victor, Kitching, Matthew, Laars, Marju, Board, Johnathan, Patel, Jignesh & Gan, Wei (2018). Directed Remote Lateral Metalation: Highly Substituted 2-Naphthols and BINOLs by in situ Directing Group Generation. Angewandte Chemie 130(30): 9569-9573, which has been published in final form at https://doi.org/10.1002/ange.201805203. This article may be used for non-commercial purposes in accordance With Wiley-VCH Terms and Conditions for self-archiving.