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
相关论文
共 1066 条
[111]   A novel atom-transfer cyclisation catalysed by indium metal in halogenated solvents [J].
Bhatti, NH ;
Salter, MM .
TETRAHEDRON LETTERS, 2004, 45 (45) :8379-8382
[112]   A Useful Synthetic Equivalent of a Hydroxyacetone Enolate [J].
Bigovic, Miljan ;
Maslak, Veselin ;
Tokic-Vujosevic, Zorana ;
Divjakovic, Vladimir ;
Saicic, Radomir N. .
ORGANIC LETTERS, 2011, 13 (17) :4720-4723
[113]   INDIUM-MEDIATED ALLYLATION OF ALDEHYDES - A CONVENIENT ROUTE TO 2-DEOXY AND 2,6-DIDEOXY CARBOHYDRATES [J].
BINDER, WH ;
PRENNER, RH ;
SCHMID, W .
TETRAHEDRON, 1994, 50 (03) :749-758
[114]   General approach to the coupling of organoindium reagents with imines via copper catalysis [J].
Black, DA ;
Arndtsen, BA .
ORGANIC LETTERS, 2006, 8 (10) :1991-1993
[115]   Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].
Bloch, R .
CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438
[116]  
Blümke T, 2010, NAT CHEM, V2, P313, DOI [10.1038/NCHEM.590, 10.1038/nchem.590]
[117]   Preparation of highly functionalized alkylzinc halides from alkyl bromides using Mg, ZnCl2 and LiCl [J].
Bluemke, Tobias D. ;
Piller, Fabian M. ;
Knochel, Paul .
CHEMICAL COMMUNICATIONS, 2010, 46 (23) :4082-4084
[118]   Palladium-catalyzed cross-methylation of aryl triflates by intramolecularly stabilized dialkyl-aluminum, -gallium and -indium reagents [J].
Blum, J ;
Katz, JA ;
Jaber, N ;
Michman, M ;
Schumann, H ;
Schutte, S ;
Kaufmann, J ;
Wassermann, BC .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2001, 165 (1-2) :97-102
[119]   NEW INDIUM-MEDIATED REACTIONS OF ENAMINES [J].
BOSSARD, F ;
DAMBRIN, V ;
LINTANF, V ;
BEUCHET, P ;
MOSSET, P .
TETRAHEDRON LETTERS, 1995, 36 (34) :6055-6058
[120]   Directed ortho insertion (DoI): A new approach to functionalized aryl and heteroaryl zinc reagents [J].
Boudet, Nadege ;
Sase, Shohei ;
Sinha, Pradipta ;
Liu, Ching-Yuan ;
Krasovskiy, Arkady ;
Knochel, Paul .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (41) :12358-+