Advanced organic reactions by Stuart W.

By Stuart W.

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REDUCTIONS Carey & Sundberg Chapter 5 problems: 1a,b,c,d,f,h,j; 2; 3a-g, n,o; 4b,j,k,l; 9; 11; Smith: Chapter 4 March: Chapter 19 30 Reductions 1. Hydrogenation 2. Boron Reagents 3. Aluminium Reagents 4. Tin Hydrides 5. Silanes 6. Dissolving Metal Reductions Hydrogenations Heterogeneous Catalytic Hydrogenation Transition metals absorbed onto a solid support metal: Pd, Pt, Ni, Rh support: Carbon, alumina, silica solvent: EtOH, EtOAc, Et2O, hexanes, etc. - Reduction of olefins & acetylenes to saturated hydrocarbons.

1995, 95, 1229. JOC 1991, 56 , 678; JOC 1988, 53 , 3641; JACS 1987, 109 , 5267 Ph2SiH2 / Et3B / Air TL 1990, 31 , 4681; TL 1991, 32 , 2569 - hypophosphorous acid as radical chain carrier JOC 1993, 58, 6838 REDUCTIONS - Photosensitized electron transfer deoxygenation of m-trifluoromethylbenzoates JACS 1986, 108, 3115, JOC 1996, 61, 6092, JOC 1997, 62, 8257 iPr iPr O O Si U N-methylcarbazole, hν, iPrOH, H2O O Si O iPr iPr O iPr iPr (85%) O Si O CF3 O U O Si O iPr iPr Dissolving Metal : JACS 1972, 94, 5098 O OH O nBuLi, (Me2N)2P(O)Cl O P(NMe2)2 Li, EtNH2, THF, tBuOH O O H CH3 O O H O Radical Decarboxylation: Barton esters Aldrichimica Acta 1987, 20 (2), 35 S hn or ∆ N S R N nBu3SnH, ∆ O O R - CO2 Radical Deamination Comprehensive Organic Synthesis 1991, vol.

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. OH O CO 2Me CO 2Me NaBH 4/ CeCl3 EtOH, H2O CHO CHO O CeCl 3 H2O 1) NaBH 4, CeCl3 2) work-up R JACS 1979, 101 , 5848 OH OH O OH CHO NaBH 4/ CeCl3 EtOH, H2O (78%) CHO REDUCTIONS Zinc Borohydride Zn(BH4)2 Synlett 1993, 885.

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