Directed Ortho Metalation Methodology. The N,N-Dialkyl Aryl O-Sulfamate as a New Directed Metalation Group and Cross-Coupling Partner for Grignard Reagents

The ortho metalation (RLi/THF/−93 °C) of 3 followed by quench with a variety of electrophiles constitutes a new general route to substituted aryl O-sulfamates 4a−k. The Kumada−Corriu cross-coupling of O-sulfamates 4e, 4n−s, and 6a with Grignard reagents gives biaryls 9a−m, and the use of 2-halo and...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2005-06, Vol.7 (13), p.2519-2522
Main Authors: Macklin, Todd K, Snieckus, Victor
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The ortho metalation (RLi/THF/−93 °C) of 3 followed by quench with a variety of electrophiles constitutes a new general route to substituted aryl O-sulfamates 4a−k. The Kumada−Corriu cross-coupling of O-sulfamates 4e, 4n−s, and 6a with Grignard reagents gives biaryls 9a−m, and the use of 2-halo and boron derivatives 4h, 4i, and 4k for Suzuki−Miyaura cross-coupling and generation of benzynes leads to naphthols 7a and 7b. A relative metalation ranking of the OSONEt2 is reported.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol050393c