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O Br O [(Ph3P)CuH] 6, THF TL 1990, 31 , 3237 Silyl Hydrides - Hydrosilylation Et3SiH + (Ph3P)3RhCl (cat) - selective 1,4-reduction of enones, 1,2-reduction of saturated ketones to alchohols. O Et3SiH, (Ph3P)3RhCl (cat) O SiEt3 H3O + O TL 1972, 5085 J. Organomet. Chem. 1975, 94 , 449 O O O iPr3SiH, Et2O Si O 2 Pt 2 OSi(iPr)3 O JOC 1994, 59, 2287 O (87%) - Buchwald Reduction JACS 1991, 113 , 5093 - catalytic reagent prepared from Cp2TiCl2 + nBuLi and stoichometric (Et)3SiH in THF will reduce ester, ketones and aldehydes to alcohols under very mild conditions.

1990, 20, 907 LiEt3BH reduces ketones, aldehydes, esters, epoxides and R-X Li s-Bu3BH reduces ketones, aldehydes, esters and epoxides (hindered borohydride) Na(CN)NH3 reduces iminium ions, ketones and aldehydes Na(AcO)3BH reduces ketones and aldehydes (less reactive) NaBH2S3 reduces ketones and aldehydes REDUCTIONS 41 Sodium Borohydride NaBH4 - reduces aldehydes and ketones to alcohols - does not react with acids, esters, lactones, epoxides or nitriles. - Additives can increase reactivity. Sodium Cyanoborohydride Na (CN)BH3 Reviews: Synthesis 1975, 136; OPPI 1979, 11 , 201 - less reactive than NaBH4 - used in reductive aminations (Borch Reduction) Na(CN)BH3 reduces iminium ions much more quickly than ketones or aldehydes R"-2NH, MeOH, AcO - NH4+ , pH~ 8 R O R R' O CHO R N R' JACS 1971, 93 , 2897 R"-2NH, MeOH, AcO- NH4+ N H Na(CN)BH3 N R' R' R R R H Na(CN)BH3 N+ N - Related to Eschweiler-Clark Reaction H2CO, HCO 2H R NH 2 R or N H Me H2CO, H2/Pd - Reduction of tosylhydrazones gives saturated hydrocarbon O H H 1) TsNHNH 2, H+ 2) Na(CN)BH3 TL 1978, 1991 (90%) H HO H HO 1) TsNHNH 2, H+ 2) Na(CN)BH3 O (100%) JOC 1977, 42 , 3157 - migration of the olefin occurs w/ α,β-unsaturated ketones O JACS 1978, 100 , 7352 (75%) - Epoxide opening O OH NaBH3CN, BF3•OEt2, THF OH HO JOC 1994, 59, 4004 NaBH2S3 REDUCTIONS Synthesis 1972, 526 Can.

Rxn. O. House Modern Synthetic Reactions, 2nd edition) R COCl R CHO R NO 2 R NH 2 R R' R R CH 2-OH R CHO R CH CH R CH 2 CH 2 R' R' O R HO H R' Ar R' R O R R' Ar CH 3 + HO R R CH 2 NH 2 R C N O R CH 2-OH R + HO R' OR' O R' R R N CH 2 R' N R' R' requires high temperature & pressure R CO 2- Na+ no reaction Raney Nickel Desulfuriztion , Reviews: Org. Rxn. 1962, 12, 356; Chem. 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.

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