2009
DOI: 10.1016/j.tet.2009.03.106
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Indium-catalyzed coupling reaction between silyl enolates and alkyl chlorides or alkyl ethers

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Cited by 28 publications
(17 citation statements)
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References 62 publications
(29 reference statements)
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“…Recently, we studied the moderate Lewis acidity of indium salts in order to develop the catalytic coupling reactions of alcohols and their derivatives with various nucleophiles [24][25][26][27][28][29][30][31][32][33][34]. Therefore, a substitution reaction in the presence of InI3 at room temperature was carried out and produced the desired thioether 3aa with a 27% yield (Entry 1).…”
Section: Resultsmentioning
confidence: 99%
“…Recently, we studied the moderate Lewis acidity of indium salts in order to develop the catalytic coupling reactions of alcohols and their derivatives with various nucleophiles [24][25][26][27][28][29][30][31][32][33][34]. Therefore, a substitution reaction in the presence of InI3 at room temperature was carried out and produced the desired thioether 3aa with a 27% yield (Entry 1).…”
Section: Resultsmentioning
confidence: 99%
“…77 The key step of the reaction mechanism involves a nucleophilic attack from the silyl enolate on a carbocation generated via Cl − abstraction (at R-Cl) by InBr 3 . Coordinative solvents quench the reaction while essentially no reaction was observed with common metalbased Lewis acids or other In(III) salts.…”
Section: Coupling Between Silyl Enolates and Alkyl Chlorides Or Alkylmentioning
confidence: 99%
“…Asymmetric Barbier-Type Propargylation with Aldehydes: Synthesis of Chiral Propargylic Alcohols Barbier-type asymmetric reactions were recently developed to access chiral enantiopure propargylic alcohols. Thus, various (S)-propargylic alcohols may be efficiently prepared via reaction of the corresponding aldehyde and propargylic bromide substrates in the presence of In(0), pyridine, and (1S,2R)-(+)-2-amino-1,2-diphenylethanol (ADPE) as a chiral auxiliary (77). 105 The best ees are observed with α-substituted aliphatic aldehydes.…”
Section: Catalysis Mediated By In(0) Metal Powdermentioning
confidence: 99%
“…4-(N-Phenyl)-sulfamoyl benzoic acid (9), prepared using a reported method 27 for the sulphonamide preparation reacting aniline and 4-(chlorosulfonyl) benzoic acid in pyridine at 0 °C and then overnight at room temperature, was reacted with 1-amino-2phenyl ethanol (5) to form the amidic bond, following the method previously quoted, producing the phenylsulfamoyl-benzamide derivative (10). The 4,5-dihydro-1,3-oxazole Heck reaction of the styrenes (2) with 1-(4-bromophenyl)-4,4-dimethylpentan-3one (15), prepared by the reaction of 1-bromo-4-(bromomethyl)benzene (13) and 1-(tertbutylvinyloxy)trimethylsilane (14) catalyzed by indium (III) bromide following methodology described by Nishimoto et al, 28 produced the ketones (16a and 16b), which were subsequently reduced to the corresponding alcohols (17a and 17b) on reaction with sodium borohydride (Scheme 3). Attempts to prepare the imidazole derivative (19b) by reaction of the alcohol (17b) using imidazole/ CDI, following our previously described methodology, led to isolation of the intermediate carbonyl imidazole (18b) only.…”
Section: Chemistrymentioning
confidence: 99%