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Simple access to elusive α-boryl carbanions and their alkylation: an umpolung construction for organic synthesis.

Hong K, Liu X, Morken JP - J. Am. Chem. Soc. (2014)

Bottom Line: The reaction of 1,1-bis(pinacolboronate) esters with alkyl halides can be effected by metal alkoxides and provides a strategy for the construction of organoboronate compounds.The reaction is found to occur by alkoxide-induced deborylation and generation of a boron-stabilized carbanion.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Merkert Chemistry Center, Boston College , Chestnut Hill, Massachusetts 02467, United States.

ABSTRACT
The reaction of 1,1-bis(pinacolboronate) esters with alkyl halides can be effected by metal alkoxides and provides a strategy for the construction of organoboronate compounds. The reaction is found to occur by alkoxide-induced deborylation and generation of a boron-stabilized carbanion.

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Deborylative Alkylation for the Construction of PhenethylamineBuilding Blocks
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sch3: Deborylative Alkylation for the Construction of PhenethylamineBuilding Blocks


Simple access to elusive α-boryl carbanions and their alkylation: an umpolung construction for organic synthesis.

Hong K, Liu X, Morken JP - J. Am. Chem. Soc. (2014)

Deborylative Alkylation for the Construction of PhenethylamineBuilding Blocks
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4353009&req=5

sch3: Deborylative Alkylation for the Construction of PhenethylamineBuilding Blocks
Bottom Line: The reaction of 1,1-bis(pinacolboronate) esters with alkyl halides can be effected by metal alkoxides and provides a strategy for the construction of organoboronate compounds.The reaction is found to occur by alkoxide-induced deborylation and generation of a boron-stabilized carbanion.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Merkert Chemistry Center, Boston College , Chestnut Hill, Massachusetts 02467, United States.

ABSTRACT
The reaction of 1,1-bis(pinacolboronate) esters with alkyl halides can be effected by metal alkoxides and provides a strategy for the construction of organoboronate compounds. The reaction is found to occur by alkoxide-induced deborylation and generation of a boron-stabilized carbanion.

Show MeSH