Synthetic methods and reactions. 136. Single-step one-carbon ring homologation of cyclic and polycyclic hydrocarbons via their methyl alcohols or carboxylic acids with sodium borohydride/triflic acid

1989 ◽  
Vol 54 (6) ◽  
pp. 1452-1453 ◽  
Author(s):  
George A. Olah ◽  
An Hsiang Wu ◽  
Omar Farooq
Keyword(s):  
Carboxylic Acids ◽  
Sodium Borohydride ◽  
Single Step ◽  
Synthetic Methods ◽  
Triflic Acid ◽  
Polycyclic Hydrocarbons ◽  
Carbon Ring

Reagents and synthetic methods. 31. Silylations with N-trimethylsilyl-2-oxazolidinone (TMSO)

1984 ◽  
Vol 62 (2) ◽  
pp. 336-340 ◽  
Author(s):  
Jesús M. Aizpurua ◽  
Claudio Palomo ◽  
Antonio L. Palomo
Keyword(s):  
Carboxylic Acids ◽  
Synthetic Methods ◽  
Triflic Acid ◽  
Points Of View

Silylation of ketones, alcohols, mercaptans, and carboxylic acids with N-trimethylsilyl-2-oxazolidinone (TMSO) and triflic acid as catalyst has been described from synthetic and mechanistic points of view.

Generation of Phosphoranyl Radicals via Photoredox Catalysis Enables Voltage–Independent Activation of Strong C–O Bonds

2018 ◽  
Author(s):  
Erin Stache ◽  
Alyssa B. Ertel ◽  
Tomislav Rovis ◽  
Abigail G. Doyle
Keyword(s):  
Carboxylic Acids ◽  
Functional Groups ◽  
Single Step ◽  
Direct Access ◽  
Photoredox Catalysis ◽  
Acyl Radical ◽  
Synthetic Strategy ◽  
Acyl Radicals ◽  
Benzyl Radicals ◽  
Aliphatic Carboxylic Acids

Alcohols and carboxylic acids are ubiquitous functional groups found in organic molecules that could serve as radical precursors, but C–O bonds remain difficult to activate. We report a synthetic strategy for direct access to both alkyl and acyl radicals from these ubiquitous functional groups via photoredox catalysis. This method exploits the unique reactivity of phosphoranyl radicals, generated from a polar/SET crossover between a phosphine radical cation and an oxygen centered nucleophile. We first show the desired reactivity in the reduction of benzylic alcohols to the corresponding benzyl radicals with terminal H-atom trapping to afford the deoxygenated product. Using the same method, we demonstrate access to synthetically versatile acyl radicals which enables the reduction of aromatic and aliphatic carboxylic acids to the corresponding aldehydes with exceptional chemoselectivity. This protocol also transforms carboxylic acids to heterocycles and cyclic ketones via intramolecular acyl radical cyclizations to forge new C–O, C–N and C–C bonds in a single step.

scholarly journals Facile reduction of intermediates from carboxylic acids and 6-nitro-1-(2-nitrophenylsulfonyloxy)benzotriazole with sodium borohydride to alcohols.

1988 ◽  
Vol 36 (9) ◽  
pp. 3628-3631 ◽  
Author(s):  
TADASHI OKAWARA ◽  
NORIHIRO IKEDA ◽  
TETSUO YAMASAKI ◽  
MITSURU FURUKAWA
Keyword(s):  
Carboxylic Acids ◽  
Sodium Borohydride
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