Stereoselective synthesis of functionalized (1E,5E)-1,5-dien-3-ynes containing ester or sulfonyl groups by palladium-catalyzed addition and cross-coupling reactions

作者：Hao, Wenyan; Xie, Shiyun; Wu, Yichao; Cai, Mingzhong^*

来源：New Journal of Chemistry, 2014, 38(6): 2686-2692.

DOI：10.1039/c4nj00087k

• CONJUGATED OLIGOENYNES
• DIYNES
• DIENYNES
• DESIGN
• ENYNE
• COMBINATION
• METATHESIS
• 1,3-DIYNES
• CHEMISTRY
• ACETYLENE

Trimethylsilylacetylene undergoes clean cis-addition to alkynyl suffones or esters 1 in the presence of catalytic palladium acetate and tri(2,6-dimethoxyphenyl)phosphine to give (E)-1-sulfonyl (or ethoxycarbonyl)-4-trimethylsilyl-substituted 1,3-enyne 2 in excellent yields. The cross-coupling reaction of (E)-1-sulfonyl (or ethoxycarbonyl)-4-trimethylsilyl-substituted 1,3-enyne 2 with (E)-alkenyl iodides 3 in the presence of Pd(PPh3)(4) and tris(diethylamino)sulfonium trimethyldifluorosilicate (TASF) affords stereoselectively (1E,5E)-1-sulfonyl (or ethoxycarbonyl)-substituted 1,5-dien-3-ynes 4 in good yields.

• 出版日期2014-6
• 单位江西师范大学