Ruthenium-Catalyzed Hydrocarboxylation of Internal Alkynes

被引:18
作者
Jeschke, Janine [1 ]
Engelhardt, Tony B. [1 ]
Lang, Heinrich [1 ]
机构
[1] Tech Univ Chemnitz, Fac Nat Sci, Inst Chem, Inorgan Chem, D-09107 Chemnitz, Germany
关键词
Homogeneous catalysis; Hydrocarboxylation; Ruthenium; Carboxylic acids; Alkynes; CARBOXYLIC-ACIDS; ENOL ESTERS; ASYMMETRIC HYDROGENATION; STEREOSELECTIVE ADDITION; MARKOVNIKOV ADDITION; SELECTIVE ADDITION; TERMINAL ALKYNES; VINYL MONOMERS; COMPLEXES; PHOTOPOLYMERIZATION;
D O I
10.1002/ejoc.201501583
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The application of the highly efficient ruthenium catalyst [Ru(CO)(2){P(p-CF3-C6H4)(3)}(2)(O2CPh)(2)] (1) in the selective synaddition of carboxylic acids to internal alkynes, yielding valuable trisubstituted enol esters with (E)-configuration, is described. All reactions feature excellent stereoselectivities and good regioselectivities. The regioselectivity is dictated by electronic and steric aspects of the alkyne substituents and the acidity of the carboxylic acid. The catalytic activity can be significantly increased by the addition of catalytic amounts of B(C6F5)(3). Relative to known catalysts for the synthesis of (E)-enol esters, this methodology offers improved selectivity and requires lower catalyst loadings. Moreover, a broad range of alkynes and carboxylic acids can be successfully converted to their corresponding (E)-enol esters in high yields.
引用
收藏
页码:1548 / 1554
页数:7
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