Organoindium Reagents: The Preparation and Application in Organic Synthesis

被引:246
作者
Shen, Zhi-Liang [2 ]
Wang, Shun-Yi [2 ]
Chok, Yew-Keong [2 ]
Xu, Yun-He [1 ,2 ]
Loh, Teck-Peng [1 ,2 ]
机构
[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China
[2] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
关键词
INDIUM-MEDIATED ALLYLATION; CROSS-COUPLING REACTIONS; ONE-POT SYNTHESIS; BARBIER-TYPE ALLYLATION; BAYLIS-HILLMAN ADDUCTS; IODIDE-PROMOTED CLEAVAGE; METHYLENE-GAMMA-BUTYROLACTONES; FRIEDEL-CRAFTS ALKENYLATION; RING-OPENING REACTION; C-BOND FORMATION;
D O I
10.1021/cr300051y
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Indium and organoindium reagents have gathered attention from the synthetic community. The unique reactivity of organoindium reagent as well as its mildness when compared to other reactive organometallic species allow substrates possessing important yet sensitive functional groups to be used directly without pre-derivatization, thus rendering organic transformations more straightforward, efficient, and economical. In addition, the feasibility of using organoindium reagents in aqueous media permits the direct functionalization of water-soluble substrates including carbohydrates and other biomolecules, which is also in accordance with the principles of green chemistry. The specific characteristics of organoindium reagent also enable organic reactions to proceed with unprecedented chemoselectivity, which is unattainable by using traditional organometallic reagents. Therefore, organoindium reagents have increasingly found utility in the assembly of complex molecules including natural products.
引用
收藏
页码:271 / 401
页数:131
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