Directed Ortho Metalation Methodology. The N , N -Dialkyl Aryl O -Sulfamate as a New Directed Metalation Group and Cross-Coupling Partner for Grignard Reagents
2005; American Chemical Society; Volume: 7; Issue: 13 Linguagem: Inglês
10.1021/ol050393c
ISSN1523-7060
AutoresTodd K. Macklin, Victor Snieckus,
Tópico(s)Asymmetric Synthesis and Catalysis
Resumo[reaction: see text] The ortho metalation (RLi/THF/-93 degrees 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 OSONEt(2) is reported.
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