Highly Stereo- and Regioselective Hydrostannylation of Internal Alkynes Promoted by Simple Boric Acid in Air
Facile hydrostannylation of alkynes in air: The ability to prepare vinylstannanes of high regio‐ and sterochemical fidelity in a safe manner employing a simple operational set up, especially on a large scale, has remained elusive. This study has shown that all of the autoxidation products of Et3B an...
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Published in | Chemistry : a European journal Vol. 18; no. 35; pp. 10821 - 10824 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
Weinheim
WILEY-VCH Verlag
27.08.2012
WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc |
Subjects | |
Online Access | Get full text |
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Summary: | Facile hydrostannylation of alkynes in air: The ability to prepare vinylstannanes of high regio‐ and sterochemical fidelity in a safe manner employing a simple operational set up, especially on a large scale, has remained elusive. This study has shown that all of the autoxidation products of Et3B and boronic acids are capable of promoting hydrostannylation. Most importantly, simple boric acid itself can also promote the hydrostannylation of highly functionalized internal alkynes with complete selectivity under very mild conditions (RT to 80 °C) in air. |
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Bibliography: | NSERC (Canada) ArticleID:CHEM201202100 ark:/67375/WNG-L5D4LHHL-H The Ontario Research Fund (ORF) istex:74255998DADB7DD799849C1C11582B658387AE31 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0947-6539 1521-3765 |
DOI: | 10.1002/chem.201202100 |