The chemistry of organoborates. Part I. New, high yield ketone syntheses by reaction of trialkylcyanoborates with acylating agents or N-phenylbenzimidoyl chloride
The chemistry of organoborates. Part I. New, high yield ketone syntheses by reaction of trialkylcyanoborates with acylating agents or N-phenylbenzimidoyl chloride
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有机硼酸盐的化学。
DOI：
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发表时间：
1975
期刊：
影响因子：
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通讯作者：
K. Rowe
中科院分区：
文献类型：
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作者：
A. Pelter;Keith Smith;M. G. Hutchings;K. Rowe
从有机硼酸盐化学的一般考虑，很明显，有机氰基硼酸盐与亲电试剂的反应具有突出的合成潜力。酰化反应的研究表明，三烷基氰基硼酸酯在低温下与三氟乙酸酐反应，在室温下与N-苯基苯甲亚胺酰氯反应，在升温下与苯甲酰氯反应，得到环状中间体，其在氧化时以优异的产率得到酮。与有机硼烷的羰基化相比，这种一锅法合成可以应用于1，1，2-三甲基丙基（己基）衍生物，而不需要特殊的条件。稠合和桥连多环酮以及官能化和不对称酮的合成的实例表明了反应的范围。
From general considerations of the chemistry of organoborates it is clear that the reactions of organocyanoborates with electrophilic reagents have outstanding synthetic potential. The acylation reactions have been studied and it is shown that trialkylcyanoborates react with trifluoroacetic anhydride at low temperatures, with N-phenylbenzimidoyl chloride at room temperature, and with benzoyl chloride on warming to give cyclic intermediates which on oxidation give ketones in excellent yields. In contrast to the carbonylation of organoboranes this one-pot synthesis can be applied to 1,1,2-trimethylpropyl (thexyl) derivatives without the need for special conditions. Examples of the synthesis of fused and bridged polycyclic ketones and of functionalised and unsymmetrical ketones indicate the scope of the reaction.