Stereoselective Copper-Catalyzed Cross-Coupling of α-CF3-Allylboronic Acids with Diazoketones
Tautvydas Kireilis, Kálmán J. Szabó
TL;DR
A copper-catalyzed reaction forms a specific carbon-carbon bond with high selectivity but has low yield.
Contribution
A stereoselective method for forming C(sp3)–C(sp3) bonds using α-CF3-allylboronic acids and diazoketones.
Findings
The reaction shows excellent regioselectivity and stereoselectivity via allylic rearrangement.
A new allylic C(sp3)–C(sp3) bond is formed efficiently.
The reaction suffers from poor yield, limiting its practicality.
Abstract
We have studied copper-catalyzed cross-coupling of chiral α-CF3-substituted allylboronic acids with α-diazoketones. The reaction proceeds with excellent regioselectivity and stereoselectivity via allylic rearrangement. The method is useful for formation a new allylic C(sp3)–C(sp3) bond with high selectivity. The poor yield is a limitation of this reaction.
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Taxonomy
TopicsFluorine in Organic Chemistry · Cyclopropane Reaction Mechanisms · Catalytic Cross-Coupling Reactions