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

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 com...

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Published in:Tetrahedron letters 2012-09, Vol.53 (37), p.4938-4941
Main Authors: Izgu, Enver Cagri, Hoye, Thomas R.
Format: Article
Language:English
Subjects:
Aniline
Aromatic compounds
Chemical reactions
Cross coupling
Halides
Joining
Organostannanes
Ortho-metalation
Tetrahedrons
Utilities
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description 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.
doi_str_mv 10.1016/j.tetlet.2012.06.138
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subjects Aniline
Aromatic compounds
Chemical reactions
Cross coupling
Halides
Joining
Organostannanes
Ortho-metalation
Tetrahedrons
Utilities
title o-(Trialkylstannyl)anilines and their utility in Migita–Kosugi–Stille cross-coupling: direct introduction of the 2-aminophenyl substituent
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