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Synfacts 2016; 12(3): 0289
DOI: 10.1055/s-0035-1561257
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Catalytic Conjunctive Cross-Coupling

Contributor(s):
Paul Knochel
,
Diana Haas
Zhang L, Lovinger GJ, Edelstein EK, Szymaniak AA, Chierchia MP, Morken JP * Boston College, Chestnut Hill, USA
Catalytic Conjunctive Cross-Coupling Enabled by Metal-Induced Metallate Rearrangement.

Science 2016;
351: 70-74
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Further Information

Publication History

Publication Date:
16 February 2016 (online)

 
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Key words

cross-coupling - metallate rearrangement

Significance

Morken and co-workers report a catalytic conjunctive cross-coupling of organoborates, organolithium reagents and organotriflates for the synthesis of chiral boronic acids with high enantioselectivity.


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Comment

The intermediate boronic ester ate-complex reacts in a palladium-induced metallate rearrangement, wherein 1,2-migration of an alkyl or aryl group from the boron atom to the vinyl α-carbon occurs simultaneously with C–Pd σ-bond formation.


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