期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 352, 期 2-3, 页码 478-492出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900836
关键词
carbonylation; carboxylic esters; DFT calculations; organoboron compounds; palladium catalysts
资金
- MEXT [20350045, 20037018]
- Grants-in-Aid for Scientific Research [20350045, 20037018] Funding Source: KAKEN
Methoxycarbonylation of aryl- and alkenyylboron Compounds was performed using the palladium(II) acetate/triphenylphosphine [Pd(OAc)(2)/PPh3] catalyst with p-benzoquinone as a stoichiometric oxidant in methanol at ambient temperature to obtain the corresponding methyl esters in good yields. A wide variety of functional groups including various carbonyl functionalities, nitrile, nitro. sulfone, and unprotected pyrrole rings were tolerated in the methoxycarbonlation, while the use of higher alcohols except for tert-butanol afforded various p-chlorobenzoates in moderate to high yields. The catalytic alkoxycarbonylation proceeded without any acid or base additive, and an oxidative transmetalation step is proposed to explain the exceptional efficacy of this protocol. DFT and MP2 calculations support the proposed mechanism.
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