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Simple Access to Elusive α-Boryl Carbanions and Their Alkylation: An Umpolung Construction for Organic Synthesis

Kai Hong, Xun Liu and James P. Morken*

*Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States, Email:

K. Hong, X. Liu, J. P. Morken, J. Am. Chem. Soc., 2014, 136, 10581-10584.

DOI: 10.1021/ja505455z

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The reaction of 1,1-bis(pinacolboronate) esters with alkyl halides promoted by metal alkoxides provides organoboronate compounds via alkoxide-induced deborylation and generation of a boron-stabilized carbanion.

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Key Words

alkylation, alkylboronates

ID: J48-Y2014