关键词: 贫电子炔烃, 叔膦, 顺式卤氢化, 亲核试剂, 过渡金属络合物, 配体, 插入反应, 环化, 催化反应, 不对称反应, 炔烃P, 合成法

Synthetic methodologies derived from electron-deficient alkynes studied by our group in recent 15 years are described. The discussions are divided into four parts: (1) tertiary phosphine triggered reactions, (2) cis-hydrohalo-genation reaction of electron- deficient alkynes, (3) protonolysis reaction of the carbon-palladium bond, (4) divalent palladium catalyzed aymmetric cyclization of enyne esters. These four parts of reactions can be divided into two types: the first is the reactions initiated only by the attack of nucleophiles on the electron- deficient alkynes; the second is the reactions initiated by the attack of the nucleophiles on the transition-metal coordinated alkynes. Detailed discussions are concentrated on the story of the discovery of the reaction, the deeper study of the research, the inquiry of the reaction mechanism and the development of the rules of the elementary reaction.

Key words: TERTIARY PHOSPHINE, NUCLEOPHILIC REAGENTS, TRANSITION METAL COMPLEX, LIGANDS, INSERTION REACTION, CYCLIZATION, CATALYTIC REACTION, ALKYNE P, SYNTHESIS METHODS