Ruthenium(II)-catalyzed cross-dehydrogenative C-H alkenylations by triazole assistance

被引:47
|
作者
Tirler, Carina [1 ]
Ackermann, Lutz [1 ]
机构
[1] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
基金
欧洲研究理事会;
关键词
C-H activation; Mechanism; Olefination; Ruthenium; Triazoles; CATALYZED DIRECT ARYLATIONS; BOND ACTIVATION; CLICK CHEMISTRY; 1,3-DIPOLAR CYCLOADDITIONS; CONJUGATE ADDITION; TERMINAL ALKYNES; FUNCTIONALIZATION; METAL; 1,2,3-TRIAZOLES; CARBOXYLATE;
D O I
10.1016/j.tet.2015.02.033
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ruthenium(II) carboxylate complexes allowed for efficient cross-dehydrogenative alkenylations of N-aryl-1,2,3-triazoles. The twofold C-H functionalizations occurred with excellent chemo-, regio-, site- and diastereoselectivities, and ample substrate scope. The versatile ruthenium(II) catalyst proved tolerant of moisture, air, and various electrophilic functional groups. Mechanistic studies were in good agreement with an initial C-H metalation by a cationic ruthenium(II) carboxylate, along with a subsequent migratory insertion of the olefin. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4543 / 4551
页数:9
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