O-(Trialkylstannyl)anilines and their utility in Migita-Kosugi-Stille cross-coupling: Direct introduction of the 2-aminophenyl substituent

Enver Cagri Izgu, Thomas R. Hoye

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11 Scopus citations

Abstract

We have developed shelf- and air-stable ortho-stannylated aniline reagents that can directly be coupled with alkenyl and aryl halides via Migita-Kosugi-Stille cross-coupling. We report (i) the efficient preparation of o-(tributylstannyl)aniline (2a) and o-(trimethylstannyl)aniline (2b), (ii) the comparison of the reactivities of 2a and 2b with those of related organostannanes in cross-coupling reaction with an alkenyl halide, and (iii) the cross-coupling of 2a and 2b with a series of arylhalides and triflate.

Original languageEnglish (US)
Pages (from-to)4938-4941
Number of pages4
JournalTetrahedron Letters
Volume53
Issue number37
DOIs
StatePublished - Sep 12 2012

Bibliographical note

Funding Information:
These studies were supported by the National Institute of General Medical Sciences (GM-65597) and the National Cancer Institute (CA-76497) of the United States National Institutes of Health.

Copyright:
Copyright 2012 Elsevier B.V., All rights reserved.

Keywords

  • Aniline
  • Cross-coupling
  • Organostannanes
  • Ortho-metalation

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