SYNTHESIS AND CHARACTERIZATION OF LITHIUM AMINOBOROHYDRIDES - A NEW CLASS OF POWERFUL REDUCING AGENTS

被引:50
作者
FISHER, GB [1 ]
HARRISON, J [1 ]
FULLER, JC [1 ]
GORALSKI, CT [1 ]
SINGARAM, B [1 ]
机构
[1] UNIV CALIF SANTA CRUZ,DEPT CHEM & BIOCHEM,SANTA CRUZ,CA 95064
关键词
D O I
10.1016/S0040-4039(00)61305-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Lithium aminoborohydrides (LiABH3), obtained by the reaction of n-BuLi with amine-boranes, are powerful reducing agents, comparable to lithium aluminum hydride, yet selective in their reducing properties. LiABH3's reduce esters, lactones, and anhydrides to the corresponding alcohols, while carboxylic acids are not reduced. Test reductions show that LiABH3's also reduce a wide range of functional groups, including amides, epoxides, oximes, nitriles, and halides.
引用
收藏
页码:4533 / 4536
页数:4
相关论文
共 20 条
[1]   A SCALE OF ELECTRONEGATIVITY BASED ON ELECTROSTATIC FORCE [J].
ALLRED, AL ;
ROCHOW, EG .
JOURNAL OF INORGANIC & NUCLEAR CHEMISTRY, 1958, 5 (04) :264-268
[2]   POTASSIUM TRI-ISOPROPOXYBOROHYDRIDE - NEW MILD COMPLEX HYDRIDE REDUCING AGENT WITH HIGH STEREOSELECTIVITY FOR REDUCTION OF KETONES [J].
BROWN, CA ;
KRISHNAM.S ;
KIM, SC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (12) :391-391
[3]   SELECTIVE REDUCTIONS .33. POTASSIUM TRIISOPROPOXYBOROHYDRIDE AS A SELECTIVE REDUCING AGENT IN ORGANIC-SYNTHESIS - REACTION WITH SELECTED ORGANIC-COMPOUNDS CONTAINING REPRESENTATIVE FUNCTIONAL-GROUPS [J].
BROWN, HC ;
CHA, JS ;
NAZER, B ;
KIM, SC ;
KRISHNAMURTHY, S ;
BROWN, CA .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (05) :885-892
[4]   INVESTIGATIONS IN THE SYNTHESIS OF ALKYL-SUBSTITUTED BOROHYDRIDES [J].
BROWN, HC ;
SINGARAM, B ;
SINGARAM, S .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1982, 239 (01) :43-64
[5]   THE PREPARATION OF SODIUM TRIISOPROPOXYBOROHYDRIDE AND TRI-TERT-BUTOXYBOROHYDRIDE - THE EFFECT OF ALKOXY SUBSTITUENTS ON THE REDUCING PROPERTIES OF BOROHYDRIDE ION [J].
BROWN, HC ;
MEAD, EJ ;
SHOAF, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (15) :3616-3620
[6]  
BROWN HC, 1953, J AM CHEM SOC, V73, P6263
[7]  
CAPKA M, 1969, COLLECT CZECH CHEM C, V34, P118
[8]  
CERNY V, 1969, C CZECH CHEM COMM, V34, P1025
[9]   EFFECT OF ALKYL SUBSTITUTION ON BORON-11 CHEMICAL SHIFTS IN AMINOBORANES AND BORATES [J].
DAVIS, FA ;
TURCHI, IJ ;
GREELEY, DN .
JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (09) :1300-&
[10]  
FISHER GB, UNPUB J AM CHEM SOC