59965-06-9Relevant articles and documents
Highly-chemoselective step-down reduction of carboxylic acids to aromatic hydrocarbons: Via palladium catalysis
Liu, Chengwei,Qin, Zhi-Xin,Ji, Chong-Lei,Hong, Xin,Szostak, Michal
, p. 5736 - 5742 (2019/06/18)
Aryl carboxylic acids are among the most abundant substrates in chemical synthesis and represent a perfect example of a traceless directing group that is central to many processes in the preparation of pharmaceuticals, natural products and polymers. Herein, we describe a highly selective method for the direct step-down reduction of carboxylic acids to arenes, proceeding via well-defined Pd(0)/(ii) catalytic cycle. The method shows a remarkably broad substrate scope, enabling to direct the classical acyl reduction towards selective decarbonylation by a redox-neutral mechanism. The utility of this reaction is highlighted in the direct defunctionalization of pharmaceuticals and natural products, and further emphasized in a range of traceless processes using removable carboxylic acids under mild, redox-neutral conditions orthogonal to protodecarboxylation. Extensive DFT computations were conducted to demonstrate preferred selectivity for the reversible oxidative addition and indicated that a versatile hydrogen atom transfer (HAT) pathway is operable.
Synthesis of (2RS,4'R,8'R)-α-tocopherol and related compounds via a 2-chlorochroman
Cohen,Schaer,Scalone
, p. 5783 - 5785 (2007/10/02)
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Total synthesis of all eight stereoisomers of α-tocopheryl acetate. Determination of their diastereoisomeric and enantiomeric purity by gas chromatography
Cohen,Scott,Neukom,et al.
, p. 1158 - 1173 (2007/10/02)
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