"Cut and Sew" Transformations via Transition-Metal-Catalyzed Carbon-Carbon Bond Activation

被引:393
作者
Chen, Peng-hao [1 ]
Billett, Brent A. [2 ]
Tsukamoto, Tatsuhiro [2 ]
Dong, Guangbin [2 ]
机构
[1] Univ Texas Austin, Dept Chem, 100 East 24th St, Austin, TX 78712 USA
[2] Univ Chicago, Dept Chem, 5735 South Ellis Ave, Chicago, IL 60637 USA
关键词
cut and sew; transition-metal catalysis; carbon-carbon activation; oxidative addition; reductive elimination; C-C-BOND; 3+2 CYCLOADDITION REACTION; RH(I)-CATALYZED (5+2)+1 CYCLOADDITION; AMINO-SUBSTITUTED CYCLOPROPANES; NATURAL-PRODUCT SYNTHESIS; ETHYL CYCLOPROPYLIDENEACETATE; ENE-VINYLCYCLOPROPANES; PHOSPHINE COMPLEXES; FORMAL SYNTHESIS; INTRAMOLECULAR CYANOAMIDATION;
D O I
10.1021/acscatal.6b03210
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The transition-metal-catalyzed "cut and sew" transformation has recently emerged as a useful strategy for preparing complex molecular structures. After oxidative addition of a transition metal into a carbon-carbon bond, the resulting two carbon termini can be both functionalized in one step via a following migratory insertion and reductive elimination with unsaturated units, such as alkenes, alkynes, allenes, CO, and polar multiple bonds. Three- or four-membered rings are often employed as reaction partners due to their high ring strains. The participation of nonstrained structures generally relies on cleavage of a polar carbon-CN bond or assistance of a directing group.
引用
收藏
页码:1340 / 1360
页数:21
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