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BF3·OEt2-Promoted Concise Synthesis of Difluoroboron-Derivatized Curcumins from Aldehydes and 2,4-Pentanedione.

ABSTRACT: A concise and one-pot cascade method has been developed to achieve the synthesis of difluoroboron-derivatized curcumins (BF2C). Treatment of 2,4-pentanedione with BF3·OEt2, followed by condensation with aldehydes in the presence of tributyl borate and butylamine at 65 °C in toluene furnished the corresponding symmetric (s-BF2C) and unsymmetric difluoroboron-derivatized curcumins (us-BF2C) in good (60 - 99%) and moderate yields (23 - 42%) within 6 - 12 h, respectively.

SUBMITTER: Liu K

PROVIDER: S-EPMC3607379 | biostudies-literature | 2013 Apr

REPOSITORIES: biostudies-literature

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BF3·OEt2-Promoted Concise Synthesis of Difluoroboron-Derivatized Curcumins from Aldehydes and 2,4-Pentanedione.

Liu Kai K Chen Jiangmin J Chojnacki Jeremy J Zhang Shijun S

Tetrahedron letters 20130213 16

A concise and one-pot cascade method has been developed to achieve the synthesis of difluoroboron-derivatized curcumins (BF2C). Treatment of 2,4-pentanedione with BF3·OEt2, followed by condensation with aldehydes in the presence of tributyl borate and butylamine at 65 °C in toluene furnished the corresponding symmetric (s-BF2C) and unsymmetric difluoroboron-derivatized curcumins (us-BF2C) in good (60 - 99%) and moderate yields (23 - 42%) wit ...[more]

PMID: 23538780

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