Advanced Organic Reactions by Rizzo C.J.

By Rizzo C.J.

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Res. (S) 1981, 17 R4N BH4 organic soluble borohydride (CH2Cl2) R4N= BnEt3N or Bu4N Heterocylces 1980, 14, 1437, 1441 reduction of amides to amines reduction of nitriles to amines BnEt3N BH4 / Me 3SiCl reduction of carbolxylic acids to alcohols LiBH4/ Me 3SiCl Synth. Commun. 1990, 20, 907 ACIEE 1989, 28, 218. Alkyl Borohydrides Selectrides M + HB 3 M + = Li (L-selectride) K (K-selectride) LS-selectride Li + HB 3 - hindered reducing agent increased selectivity based on steric considerations CO 2H O CO 2H OH L-selectride THF JACS 1971, 93, 1491 R R HO HO OH OH REDUCTIONS 45 - selective 1,4-reductions of α,β-unsaturated carbonyl cmpds.

Rev. 1962, 62, 347. R R S R Raney Nickel R H R H (CH 2)n O R S 31 REDUCTIONS O O O O O HO 32 O HO Raney Nickel JOC 1987, 52, 3346 EtOH (74%) H S H S Homogeneous Catalytic Hydrogenation - catalyst is soluble in the reaction medium - catalyst not "poisoned" by sulfur - very sensitive to steric effects - terminal olefins faster than internal; cis olefins faster than trans R R > > R R R R > R R R > R R >> R R R - (Ph3P)3RhCl (Wilkinson's Catalyst); [R3P Ir(COD)py]+ PF6- (Crabtree's Catalyst) (Ph3P)3RhCl, H2 OH OH JOC 1992, 57, 2767 C 6H6 (92%) Directed Hydrogenation Review: Angew.

1981, 29 , 1159; Chem. Ber. 1984, 117 , 856. Ar-NO2 → Ar-NH2 Ar-NO → Ar- NH2 R2C=N-OH → R2CH-NH2 NaBH4 / TiCl 4 Synthesis 1980, 695. R-COOH → R-CH2-OH R-COOR' → R-CH2-OH R-CN → R-CH2-NH2 R-CONH2 → R-CH2-NH2 R2C=N-OH → R2CH-NH2 R-SO2-R' → R-S-R' NaBH4 / CeCl 3 Luche Reduction reduced α,β-unsaturated ketones in a 1,2-fashion OH NaBH 4/ CeCl3 R R NaBH 4 R R O OH O R + R R R R R R H R JCSCC 1978, 601 JACS 1978, 100 , 2226 O OH CO 2Me NaBH 4/ CeCl3 C 5H11 CO 2Me MeOH C 5H11 OH OH - selective reduction of ketones in the presence of aldehydes.

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