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...

Full description

Saved in:
Bibliographic Details
Published inChemistry : a European journal Vol. 18; no. 35; pp. 10821 - 10824
Main Authors Oderinde, Martins S., Hunter, Howard N., Froese, Robert D. J., Organ, Michael G.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 27.08.2012
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
Subjects
Alkynes
Autoxidation
boric acid
Boric acids
borinate
boronate
catalysis
Chemistry
Chemistry, Multidisciplinary
hydrostannylation
Physical Sciences
Science & Technology
Selectivity
boric acid
hydrostannylation
PH3SNH
ACETYLENES
borinate
MECHANISM
HYDROSILYLATION
catalysis
ALCOHOLS
boronate
HYDROSTANNATIONS
ET3B
CYCLIZATION
Online AccessGet full text

Cover

More Information
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.
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