Advanced Organic Reactions by Rizzo C.J. PDF

By Rizzo C.J.

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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. e. hydroxyls, can sometimes direct the delivery of H2. Cis addition of H2. R1 R1 R2 R2 H H2, Pd/C R1 H R2 R1 R2 - Catalyst can be "poisoned" - Directed heterogeneous hydrogenation O O H H2, Pd/C O O OH MeO O OH MeO H2, Pd/C H O O CO2Me MeO O CO2M2 (86 : 14) MeO Lindlar Catalyst ( Pd/ BaSO4/ quinoline)- partially poisoned to reduce activity; will only reduce the most reactive functional groups.

1988, 18 , 89. - even greater 1,4-selectivity Li + HBEt3 (Super Hydride) - very reactive hydride source - reduces ketones, aldehydes, esters, epoxides and C-X (alkyl halides and sulfonates) O HO Li Et3BH, THF HO HCA 1983, 66 , 760 HO H H HO HO CH 3 OH HO 1) TsCl, pyridine 2) Li Et3BH, THF HCA 1988, 71 , 872 HO H H Boranes Hydroboration H2O 2, NaOH B 2H6 B R R' R B 2H6 R' B R B 2H6 H HO H H H3O + H R B H2O 2, NaOH R R' H H R-CH 2CHO H - BH3 reduces carboxylic acids to 1° alcohols in the presence of esters, nitro and cyano groups.

Boron Hydrides Review: Chem. Rev. 1986, 86 , 763. NaBH4 reduces ketones and aldehydes LiBH4 reduces ketones, aldehydes, esters and epoxides. THF soluble LiBH4/TMSCl stronger reducing agent. ACIEE 1989, 28, 218. Zn(BH4)2 reduces ketones and aldehydes R4N BH4 organic soluble (CH2Cl2) borohydrides. Synth Commun. 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.

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Advanced Organic Reactions by Rizzo C.J.


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