180295-26-5Relevant articles and documents
N-Heterocyclic Carbene-Catalyzed Decarboxylative Alkylation of Aldehydes
Ishii, Takuya,Kakeno, Yuki,Nagao, Kazunori,Ohmiya, Hirohisa
supporting information, p. 3854 - 3858 (2019/04/25)
We found that N-heterocyclic carbene catalysis promoted the unprecedented decarboxylative coupling of aryl aldehydes and tertiary or secondary alkyl carboxylic acid-derived redox-active esters to produce aryl alkyl ketones. The mild and transition-metal-free reaction conditions are attractive features of this method. The power of this protocol was demonstrated by the functionalization of pharmaceutical drugs and natural product. A reaction pathway involving single electron transfer from an enolate form of Breslow intermediate to a redox ester followed by recombination of the resultant radical pair to form a carbon-carbon bond is proposed.
Mechanism and scope of the cyanide-catalyzed cross silyl benzoin reaction
Linghu, Xin,Bausch, Cory C.,Johnson, Jeffrey S.
, p. 1833 - 1840 (2007/10/03)
In this work, cross silyl benzoin addition reactions between acylsilanes (1) and aldehydes (2) catalyzed by metal cyanides are described. Unsymmetrical aryl-, heteroaryl-, and alkyl-substituted benzoin adducts can be generated in moderate to excellent yie
Efficient and chemoselective protection of alcohols and phenols with tert-butyldimethylchlorosilane (TBDMCS) under solvent-free conditions
Firouzabadi, Habib,Etemadi, Shahrad,Karimi, Babak,Jarrahpour, Ali Asghar
, p. 45 - 51 (2007/10/03)
Various types of primary and secondary alcohols and phenols can be converted efficiently to their corresponding TBDMS ethers using TBDMCS/imidazole under solvent-free conditions. Elimination of DMF, accompanied with an easy non-aqueous work-up and a high rate enhancement of the reaction are worthy to be mentioned for the presented method. The reactions show absolute chemoselectivity for the protection of primary in the presence of secondary alcohols.