Aerobic Copper-Catalyzed Organic Reactions

被引:1469
作者
Allen, Scott E. [1 ]
Walvoord, Ryan R. [1 ]
Padilla-Salinas, Rosaura [1 ]
Kozlowski, Marisa C. [1 ]
机构
[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA
基金
美国国家科学基金会;
关键词
OXIDATIVE-COUPLING POLYMERIZATION; CATECHOL-OXIDASE ACTIVITY; C-H BONDS; LIQUID-PHASE OXIDATION; FORM POLY(2,6-DIMETHYL-1,4-PHENYLENE OXIDE); ENANTIOSELECTIVE TOTAL-SYNTHESIS; BAEYER-VILLIGER OXIDATION; CARBON-CARBON BONDS; ONE-POT SYNTHESIS; COPPER(II)-CATALYZED O-PHENYLATION;
D O I
10.1021/cr300527g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Oxygen is a highly atom-economical, environmentally benign, and abundant oxidant, which makes it ideal in many ways. The high activation energies in the reactions of oxygen require that catalysts be employed. A number of alternate approaches have been developed allowing oxidation chemistry to be used safely across a broader array of conditions. For example, use of carbon dioxide instead of nitrogen as a diluent leads to reduced flammability. Alternately, water can be added to moderate the flammability allowing even pure oxygen to be employed. New reactor designs also allow pure oxygen to be used instead of diluted oxygen by maintaining gas bubbles in the solvent, which greatly improves reaction rates and prevents the build up of higher concentrations of oxygen in the head space. Oxidation occurs through two primary mechanisms. In acidic or activated substrates, deprotonation can occur, followed by single-electron oxidation to form the key radical species that then reacts with molecular oxygen.
引用
收藏
页码:6234 / 6458
页数:225
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