Alcohols in direct carbon-carbon and carbon-heteroatom bond-forming reactions: recent advances

Abstract

In recent years, nucleophilic substitution of alcohols leading to the formation of the C-C and C-heteroatom bonds has become an attractive process used in the synthesis of organic compounds, offering a potential impact on the environment, since water is the only by-product of the reaction. A comprehensive compilation of methods for the activation and displacement of a hydroxyl group covering the last seventeen years is the objective of the present review.

Efficient Thiolation of Alcohols Catalyzed by Long Chained Acid‐Functionalized Ionic Liquids under Mild Conditions

“…Interestingly, 1.64 g of the desired product was obtained with only slight decrease in yield (94 % vs. 97 %). According to previous research and the above results, [22,23] we proposed a possible mechanism for the thiolation of alcohols (Scheme 3). Carbocations may be the key intermediate.…”

“…According to previous research and the above results,, we proposed a possible mechanism for the thiolation of alcohols (Scheme ). Carbocations may be the key intermediate.…”

“…With the development of Green Chemistry, easily available and cheap alcohols are attractive sources of electrophiles and the only by‐product formed in the reaction of alcohols and thiols is water. Thus, direct nucleophilic substitution reactions of alcohols have gained much attention . Previously, we realized direct synthesis of polysubstituted olefins via construction of C‐C bonds from alcohols or alkenes with alcohols and also developed system for direct amination of alcohols , .…”

“…Thus, direct nucleophilic substitution reactions of alcohols have gained much attention. [18][19][20][21][22] Previously, we realized direct synthesis of polysubstituted olefins via construction of C-C bonds from alcohols or alkenes with alcohols and also developed system for direct amination of alcohols. [23,24] Generally, carbocations from alcohols were proposed as the active intermediates during the systems.…”

N-Halosuccinimides as Precatalysts for C-, N-, O-, and X-Nucleophilic Substitution Reactions of Alcohols under Mild Reaction Conditions

“…Many related transformations, including the use of Brønsted and Lewis acids, metal ions, or other supporters in a substoichiometric amount, have been reported by several reviews [3][4][5][6][7][8][9][10][11][12][13] and recent related advanced reports [14][15][16][17][18]. However, the requirement of toxic or expensive reagents, environmentally undesirable solvents, a high concentration of the mediator, prolonged reaction time, or high temperature make such a method less attractive from the green chemical aspect.…”