63224-18-0Relevant articles and documents
Late-Stage β-C(sp3)-H Deuteration of Carboxylic Acids
Mal, Sourjya,Uttry, Alexander,Van Gemmeren, Manuel
supporting information, p. 10895 - 10901 (2021/08/03)
Carboxylic acids are highly abundant in bioactive molecules. In this study, we describe the late-stage β-C(sp3)-H deuteration of free carboxylic acids. On the basis of the finding that C-H activation with our catalysts is reversible, the de-deuteration process was first optimized. The resulting method uses ethylenediamine-based ligands and can be used to achieve the desired deuteration when using a deuterated solvent. The reported method allows for the functionalization of a wide range of free carboxylic acids with diverse substitution patterns, as well as the late-stage deuteration of bioactive molecules and related frameworks and enables the functionalization of nonactivated methylene β-C(sp3)-H bonds for the first time.
A Simple Aliphatic Diamine Auxiliary for Palladium-Catalyzed Arylation of Unactivated β-C(sp3)-H Bonds
Lou, Jiang,Wang, Quannan,He, Yuan,Yu, Zhengkun
supporting information, p. 4571 - 4584 (2018/10/25)
Palladium-catalyzed β-C(sp3)-H arylation of aliphatic acid derivatives was achieved by means of 2-dimethylaminoethylamine auxiliary as a directing group. The β-C(sp3)-H arylation reactions with aryl and heteroaryl iodides efficiently afforded the corresponding arylated hydrocinnamic acid derivatives. Direct β-C(sp3)-H alkynylation, and arene C?H arylation and alkynylation were also realized under the same or slightly modified conditions. The aliphatic diamine auxiliary in the products could be readily removed by methanol in the presence of BF3 ? OEt2. In comparison with the widely used bidentate nitrogen-containing directing groups, 2-dimethylaminoethylamine is a simple, cheap, readily available and removable, and atom-economical directing group for C?H functionalization. (Figure presented.).
A mild chemospecific reductive dehalogenation of ethylaminobenzamides with lithium aluminum hydride
Hendrix, James A.,Stefany, David W.
, p. 6749 - 6752 (2007/10/03)
A mild reduction of ortho-fluoro benzamides was discovered using LAH. The reaction proceeds cleanly and in moderate yields. The scope of the reaction is explored and a mechanism is proposed. A two carbon spacer between the amide and a 3°amine is optimal for this chelation controlled reaction.
