Synthetic applications of hydride abstraction reactions by organic oxidants

被引:31
|
作者
Miller, Jenna L. [1 ]
Lawrence, Jean-Marc I. A. [1 ]
del Rey, Freddy O. Rodriguez [1 ]
Floreancig, Paul E. [1 ]
机构
[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
基金
美国国家科学基金会;
关键词
C-H FUNCTIONALIZATION; DEHYDROGENATIVE-COUPLING CDC; CARBON BOND FORMATION; OXIDATIVE CARBOCATION FORMATION; PRINS-TYPE CYCLIZATION; DIELS-ALDER REACTIONS; STEREOSELECTIVE-SYNTHESIS; STRUCTURALLY DIVERSE; SELECTIVE OXIDATION; SECONDARY ALCOHOLS;
D O I
10.1039/d1cs01169c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Carbon-hydrogen bond functionalizations provide an attractive method for streamlining organic synthesis, and many strategies have been developed for conducting these transformations. Hydride-abstracting reactions have emerged as extremely effective methods for oxidative bond-forming processes due to their mild reaction conditions and high chemoselectivity. This review will predominantly focus on the mechanism, reaction development, natural product synthesis applications, approaches to catalysis, and use in enantioselective processes for hydride abstractions by quinone, oxoammonium ion, and carbocation oxidants. These are the most commonly employed hydride-abstracting agents, but recent efforts illustrate the potential for weaker ketone and triaryl borane oxidants, which will be covered at the end of the review.
引用
收藏
页码:5660 / 5690
页数:31
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