期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 80, 期 20, 页码 9807-9816出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01041
关键词
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资金
- EPSRC [EP/K00736X/1]
- EPSRC (DTP)
- RSC Undergraduate Research Bursary
- Heriot-Watt University
- EPSRC [EP/K00736X/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/K00736X/1] Funding Source: researchfish
A mild gold-catalyzed protodeboronation reaction, which does not require acid or base additives and can be carried out in green solvents, is described. As a result, the reaction is very functional-group-tolerant, even to acid- and base-sensitive functional groups, and should allow for the boronic acid group to be used as an effective traceless directing or blocking group. The reaction has also been extended to deuterodeboronations for regiospecific ipso-deuterations of aryls and heteroaryls from the corresponding organoboronic acid. Based on density functional theory calculations, a mechanism is proposed that involves nucleophilic attack of water at boron followed by rate-limiting B-C bond cleavage and facile protonolysis of a Au-sigma-phenyl intermediate.
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