N,N-dichloro-4-methylbenzenesulphonimide as a novel and efficient catalyst for acetylation of alcohols under mild conditions

Abstract

Álcoois de estruturas diversas foram acetilados com anidrido acético, através de reações limpas e eficientes, usando-se quantidade catalítica de N,N-dicloro-4-metilbenzenossulfonamida em diclorometano. Todas as reações ocorreram a temperatura ambiente, com rendimentos de bons a excelentes.Structurally diverse alcohols were acetylated in a clean and efficient reaction with acetic anhydride based on the use of a catalytic amount of N,N-dichloro-4-methylbenzenesulphonimide in dichloromethane. All reactions were performed at room temperature in good to excellent yields.

Application of N-halo reagents in organic synthesis

“…Recently some new N-halo sulfonamides have been reported as chemoselective brominating agents for a broad range of organic compounds (Scheme 101) [123][124][125][126][127][128][129][130][131][132]. Bromination of allylic compounds was described by using N,N'-dibromo-N,N'-ethanediylbis(2,5-dimethylbenzene)sulfonamide (Scheme 102) [134].…”

“…N,N-dibromo(p-toluenesulfonamide) and N,N-dichloro(p-toluenesulfonamide) catalyze acetylation of structurally drivers alcohols by the reaction of acetic anhydride in chloroform at room temperature (Scheme 116)[153][154]. N,N-dibromo(p-toluenesulfonamide) and N,N-dichloro(p-toluenesulfonamide) catalyze acetylation of structurally drivers alcohols by the reaction of acetic anhydride in chloroform at room temperature (Scheme 116)[153][154].…”

p-Toluenesulfonyl Chloride (p-TsCl)-Catalyzed Trimethylsilylation of Hydroxyl Groups Using Hexamethyldisilazane and Their Regeneration Under Mild Conditions: The First Example for Catalytic Application of p-Toluenesulfonyl Chloride

“…In a result of our investigations on preparation and catalytic applications of N-halogen compounds (as source of positive halogen) in organic synthesis, [30][31][32][33][34] herein for the first time we disclose the use of a catalytic amount of p-toluenesulfonyl chloride as a source of "Cl + " for efficient O-trimethylsilylation of a wide variety of hydroxyl groups Downloaded by [University of Nebraska, Lincoln] at 10:17 05 January 2015 (alcohols and phenols) using readily available HMDS and the desilylation of the corresponding TMS ethers in water (Scheme 1).…”

Boric acid as cost-effective and recyclable catalyst for trimethylsilyl protection and deprotection of alcohols and phenols

“…In our ongoing research program to develop new synthetic methodologies for protection and deprotection of organic functional groups, [27][28][29][30] we conceived that boric acid, which can generate H + in the reaction medium on reaction with alcohol or water, might be a useful catalyst for protection and deprotection of alcohols and phenols as tms ethers.…”