Fluoride-Mediated Dephosphonylation of α-Diazo-β-carbonyl Phosphonates
Fluoride-Mediated Dephosphonylation of α-Diazo-β-carbonyl Phosphonates
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DOI：
10.1021/acs.orglett.6b03573
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发表时间：
2017-01-20
期刊：
影响因子：
5.2
通讯作者：
Ramana, Chepuri V.
中科院分区：
文献类型：
--
作者：
Phatake, Ravindra S.;Mullapudi, Venkannababu;Ramana, Chepuri V.
已经提出并实施了氟化物介导的α-重氮基-β-羰基膦酸酯的选择性脱膦酰化的可能性，例如Ohira-Bestmann试剂。所得的α-重氮羰基中间体在室温下与共轭烯烃和苯炔进行（3 + 2）p环加成反应。有趣的是，在目前的条件下，所得的环加成产物经历N-酰化（与过量的α-重氮-β-羰基膦酸酯）或迈克尔加成（与共轭烯烃）。
The possibility of fluoride-mediated selective dephosphonylation of alpha-diazo-beta-carbonyl phosphonates such as the Ohira-Bestmann reagent has been proposed and executed. The resulting alpha-diazocarbonyl intermediates undergo a (3 + 2)pcycloaddition at room temperature with conjugated olefins and benzynes. Interestingly, under the current conditions, the resulting cycloaddition products underwent either N-acylation (with excess alpha-diazo-beta-carbonyl phosphonates) or Michael addition (with conjugated olefins).