1883-32-5Relevant articles and documents
A practical decarboxylative hydroxylation of carboxylic acids
Barton, Derek H. R.,Gero, Stephane D.,Holliday, Pascale,Quiclet-Sire, Beatrice,Zard, Samir Z.
, p. 6751 - 6756 (1998)
Irradiation of esters of N-hydroxy-2-thiazolinethione under air or oxygen at room temperature in the presence of tert-dodecanethiol affords the corresponding nor-alcohols after a reductive work-up.
Method for activation and recycling of trityl resins
Redwan, Itedale Namro,Gr?tli, Morten
, p. 7071 - 7075 (2012)
This note describes a rapid and mild strategy for the loading of alcohols and anilines onto a polystyrene triphenylmethyl (trityl) resin. High loadings were obtained in a matter of minutes by treating resin-bound trityl chloride with triethyloxonium tetrafluoroborate followed by alcohols or anilines. Yields were comparable or better than known literature methods. Recycling of the recovered resin was also possible using the developed method.
Primary Alcohols via Nickel Pentacarboxycyclopentadienyl Diamide Catalyzed Hydrosilylation of Terminal Epoxides
Lambert, Tristan H.,Steiniger, Keri A.
, p. 8013 - 8017 (2021/10/25)
The efficient and regioselective hydrosilylation of epoxides co-catalyzed by a pentacarboxycyclopentadienyl (PCCP) diamide nickel complex and Lewis acid is reported. This method allows for the reductive opening of terminal, monosubstituted epoxides to form unbranched, primary alcohols. A range of substrates including both terminal and nonterminal epoxides are shown to work, and a mechanistic rationale is provided. This work represents the first use of a PCCP derivative as a ligand for transition-metal catalysis.
A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions
Huang, Binbin,Guo, Lin,Xia, Wujiong
supporting information, p. 2095 - 2103 (2021/03/26)
A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.
Continuous-Flow Amide and Ester Reductions Using Neat Borane Dimethylsulfide Complex
?tv?s, Sándor B.,Kappe, C. Oliver
, p. 1800 - 1807 (2020/02/27)
Reductions of amides and esters are of critical importance in synthetic chemistry, and there are numerous protocols for executing these transformations employing traditional batch conditions. Notably, strategies based on flow chemistry, especially for amide reductions, are much less explored. Herein, a simple process was developed in which neat borane dimethylsulfide complex (BH3?DMS) was used to reduce various esters and amides under continuous-flow conditions. Taking advantage of the solvent-free nature of the commercially available borane reagent, high substrate concentrations were realized, allowing outstanding productivity and a significant reduction in E-factors. In addition, with carefully optimized short residence times, the corresponding alcohols and amines were obtained in high selectivity and high yields. The synthetic utility of the inexpensive and easily implemented flow protocol was further corroborated by multigram-scale syntheses of pharmaceutically relevant products. Owing to its beneficial features, including low solvent and reducing agent consumption, high selectivity, simplicity, and inherent scalability, the present process demonstrates fewer environmental concerns than most typical batch reductions using metal hydrides as reducing agents.
