Copper(II)-Catalyzed -Borylation of Acetylenic Esters in Water

A method for the -borylation of alkynoates has been developed. In the presence of bis(pinacolato)diboron and catalytic amounts of both copper(II) and 4-picoline, substituted alkynoates undergo borylation in a regio-, stereo-, and chemoselective fashion. The reaction is performed under mild condition...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 47; no. 15; pp. 2242 - 2248
Main Authors Peck, Cheryl L., Calderone, Joseph A., Santos, Webster L.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.08.2015
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CATALYSIS
ACTIVATION
ASYMMETRIC-SYNTHESIS
hydroboration
alkynes
EFFICIENT SYNTHESIS
ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS
BORON CONJUGATE ADDITIONS
ALKENES
stereoselectivity
copper
boron
DIBORATION
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Summary:A method for the -borylation of alkynoates has been developed. In the presence of bis(pinacolato)diboron and catalytic amounts of both copper(II) and 4-picoline, substituted alkynoates undergo borylation in a regio-, stereo-, and chemoselective fashion. The reaction is performed under mild conditions using water as solvent and open to the atmosphere to exclusively afford (Z)--boryl-,-unsaturated esters.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0034-1380524