CONVENIENT METHODS FOR THE REDUCTION OF AMIDES, NITRILES, CARBOXYLIC ESTERS, ACIDS AND HYDROBORATION OF ALKENES USING NABH4/I2 SYSTEM

被引:167
作者
PRASAD, ASB [1 ]
KANTH, JVB [1 ]
PERIASAMY, M [1 ]
机构
[1] UNIV HYDERABAD,SCH CHEM,HYDERABAD 500134,ANDHRA PRADESH,INDIA
关键词
D O I
10.1016/S0040-4020(01)81236-9
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
Reaction of amides with NaBH4-I2 system in THF gives the corresponding amines in 70-76% yields. Reduction of nitriles yields the corresponding amines in 70-75% yields. The I2/NaBH4 system is useful in the hydroboration of olefins and the corresponding alcohols are obtained in 78-92% yields after H2O2/OH- oxidation. The reagent system is also useful for the reduction of carboxylic esters and acids to the corresponding alcohols in 60-90% yields.
引用
收藏
页码:4623 / 4628
页数:6
相关论文
共 10 条
[1]
AKABORI S, 1991, J CHE MSOC P1, P482
[2]
SELECTIVE REDUCTIONS .29. A SIMPLE TECHNIQUE TO ACHIEVE AND ENHANCED RATE OF REDUCTION OF REPRESENTATIVE ORGANIC-COMPOUNDS BY BORANE-DIMETHYL SULFIDE [J].
BROWN, HC ;
CHOI, YM ;
NARASIMHAN, S .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (16) :3153-3163
[3]
A NEW TECHNIQUE FOR THE CONVERSION OF OLEFINS INTO ORGANOBORANES AND RELATED ALCOHOLS [J].
BROWN, HC ;
RAO, BCS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (21) :5694-5695
[4]
BROWN HC, 1975, ORGANIC SYNTHESES VI
[5]
FREEGUARD GF, 1965, CHEM IND-LONDON, P471
[6]
AN OPERATIONALLY SIMPLE HYDROBORATION OXIDATION EXPERIMENT [J].
KABALKA, GW ;
WADGAONKAR, PP ;
CHATLA, N .
JOURNAL OF CHEMICAL EDUCATION, 1990, 67 (11) :975-976
[7]
SELECTIVE REDUCTION OF CARBOXYLIC-ACIDS INTO ALCOHOLS USING NABH4 AND I2 [J].
KANTH, JVB ;
PERIASAMY, M .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5964-5965
[8]
CLEAVAGE OF ETHERS AND GEMINAL DIACETATES USING THE BORON TRIIODIDE-N,N-DIETHYLANILINE COMPLEX [J].
NARAYANA, C ;
PADMANABHAN, S ;
KABALKA, GW .
TETRAHEDRON LETTERS, 1990, 31 (48) :6977-6978
[9]
A SIMPLE CONVENIENT METHOD FOR THE GENERATION OF DIBORANE FROM NABH4 AND I-2 [J].
NARAYANA, C ;
PERIASAMY, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 323 (02) :145-147
[10]
A NEW REDUCTION OF SOME CARBOXYLIC ESTERS WITH SODIUM-BOROHYDRIDE AND ZINC-CHLORIDE IN THE PRESENCE OF A TERTIARY AMINE [J].
YAMAKAWA, T ;
MASAKI, M ;
NOHIRA, H .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (09) :2730-2734