Indium(I) Iodide Promoted Cleavage of Dialkyl Disulfides and Subsequent Michael Addition of Thiolate Anions to Conjugated Carbonyl Compounds.

ChemInform ◽  
2004 ◽  
Vol 35 (43) ◽  
Author(s):  
Brindaban C. Ranu ◽  
Tanmay Mandal
2006 ◽  
Vol 84 (5) ◽  
pp. 762-770 ◽  
Author(s):  
Brindaban C Ranu ◽  
Tanmay Mandal

Indium(I) iodide promotes cleavage of dialkyl disulfides generating thiolate anions that then undergo facile addition to α,β-unsaturated ketones, aldehydes, carboxylic esters, and nitriles under neutral conditions producing corresponding β-ketosulfides or β-cyanosulfides. This strategy has also been used for the regioselective nucleophilic ring opening of epoxides by thiolate anions in presence of indium(III) chloride producing corresponding β-hydroxyphenyl sulfides. The reactions are in general, very clean, high yielding, and reasonably fast. Thus, simple and convenient procedures for the synthesis of β-ketosulfides or β-cyanosulfides and β-hydroxyalkyl sulfides have been developed using this cleavage reaction.Key words: indium(I) iodide, Michael addition, β-ketosulfide, β-cyanosulfide, epoxide, β-hydroxy sulfide.


2018 ◽  
Vol 16 (6) ◽  
pp. 924-935 ◽  
Author(s):  
A. Castán ◽  
R. Badorrey ◽  
J. A. Gálvez ◽  
P. López-Ram-de-Víu ◽  
M. D. Díaz-de-Villegas

Novel bifunctional pyrrolidine-based organocatalysts applicable for the asymmetric Michael addition of aldehydes and ketones to nitroolefins have been developed.


2018 ◽  
Vol 14 ◽  
pp. 3018-3024
Author(s):  
Rudolf Knorr ◽  
Barbara Schmidt

Sterically well-shielded against unsolicited Michael addition and polymerization reactions, α-metalated α-(1,1,3,3-tetramethylindan-2-ylidene)acetonitriles added reversibly to three small aldehydes and two bulky ketones at room temperature. Experimental conditions were determined for transfer of the nucleofugal title carbanion unit between different carbonyl compounds. These readily occurring retro-additions via C–C(O) bond fission may also be used to generate different metal derivatives of the nucleofugal anions as equilibrium components. Fluoride-catalyzed, metal-free desilylation admitted carbonyl addition but blocked the retro-addition.


ChemInform ◽  
2003 ◽  
Vol 34 (13) ◽  
Author(s):  
Younes Abrouki ◽  
Mohamed Zahouily ◽  
Ahmed Rayadh ◽  
Bouchaib Bahlaouan ◽  
Said Sebti

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