A coupling of benzamides and donor/acceptor diazo compounds to form γ-lactams via Rh(III)-catalyzed C-H activation.

A coupling of benzamides and donor/acceptor diazo compounds to form γ-lactams via Rh(III)-catalyzed C-H activation.
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DOI:
10.1021/ja402274g
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发表时间:
2013-04-10
影响因子:
15
通讯作者:
Rovis, Tomislav
Rovis, Tomislav
中科院分区:
化学1区
文献类型:
--
作者:
Hyster, Todd K.;Ruhl, Kyle E.;Rovis, Tomislav

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O-新戊酰基苯并异丙酮酸与给体/受体重氮化合物偶联,得到高产率的异吲哚类化合物。该反应可以容忍广泛的苯异羟肟酸和重氮化合物,包括取代的2,2,2-三氟重氮乙烷。机理实验表明,C-H的活化是周转受限和不可逆的,而重氮化合物的插入有利于缺电子底物。
The coupling of O-pivaloyl benzhydroxamic acids with donor/acceptor diazo compounds provides iso-indolones in high yield. The reaction tolerates a broad range of benzhydroxamic acids and diazo compounds including substituted 2,2,2-trifluorodiazo ethanes. Mechanistic experiments suggest that C–H activation is turnover limiting and irreversible, while insertion of the diazo compound favors electron deficient substrates.
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