Successive Cu/Pd transmetalation relay catalysis in stereoselective synthesis of tetraarylethenes

文献情報

出版日 2015-08-06

DOI 10.1039/C5QO00205B

インパクトファクター 5.281

著者

Chuanling Song, Yihua Sun, Jianwu Wang, Hui Chen, Jiannian Yao, Chen-Ho Tung

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要旨

A new and efficient strategy for the synthesis of tetraaryl-substituted olefins has been developed. With a Cu/Pd-catalyzed isomerization/insertion/oxidative coupling cascade reaction of cyclopropene with internal alkynes, a wide variety of cis-tetrasubstituted olefins were synthesized in good yields as single stereoisomers. The photophysical properties of these novel tetraarylethenes were fully characterized and proved to be good AIE (aggregation-induced emission) luminogens. Experimental studies and theoretical calculation indicated that Cu(I) and Pd(II) were the actual catalysts. A novel deprotonative Cu-catalyzed cyclopropene cycloisomerization and subsequent successive Cu/Pd transmetalation relay mechanism was proposed for the discovered reaction.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry