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Synfacts 2014; 10(1): 0084
DOI: 10.1055/s-0033-1340371
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Trisubstituted Alkenylstannanes Starting from Alkynoates

Contributor(s):
Paul Knochel
,
Nadja M. Barl
Wakamatsu T, Nagao K, Ohmiya H, * Sawamura M. * Hokkaido University, Sapporo, Japan
Synthesis of Trisubstituted Alkenylstannanes through Copper-Catalyzed Three-Component Coupling of Alkylboranes, Alkynoates and Tributyltin Methoxide.

Angew. Chem. Int. Ed. 2013;
52: 11620-11623
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Further Information

Publication History

Publication Date:
13 December 2013 (online)

 
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Key words

tin - boron - copper - alkynoates - tributyltin methoxide - trisubstituted alkenylstannanes

Significance

The authors report a highly regio­selective copper-catalyzed synthesis of trisubstituted alkenylstannanes. Through a three-component coupling of alkylboranes, alkynoates and tributyltin methoxide, these trisubstituted alkenylstannanes are obtained in good yields and with high syn selectivity. The appropriate alkylboranes are easily accessible by hydroboration of the corresponding alkenes with the 9-borabicyclo[3.3.1]nonane (9-BBN-H) dimer.


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Comment

Standard methods for the synthesis of alkenylstannanes described by Shirakawa and ­Hiyama include the palladium- or nickel-catalyzed carbostannylation of internal alkynes with organostannanes which are somewhat difficult to prepare.


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