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Direct Borylation of Primary CH Bonds in Functionalized Molecules by Palladium Catalysis
Author(s) -
Zhang LiSheng,
Chen Guihua,
Wang Xin,
Guo QingYun,
Zhang XiSha,
Pan Fei,
Chen Kang,
Shi ZhangJie
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201310000
Subject(s) - borylation , chemistry , alkyl , palladium , molecule , primary (astronomy) , catalysis , combinatorial chemistry , organic synthesis , organic chemistry , environmentally friendly , aryl , ecology , physics , astronomy , biology
Abstract Organoborane compounds are among the most commonly employed intermediates in organic synthesis and serve as crucial precursors to alcohols, amines, and various functionalized molecules. A simple palladium‐based system catalyzes the conversion of primary C(sp 3 )H bonds in functionalized complex organic molecules into alkyl boronate esters. Amino acids, amino alcohols, alkyl amines, and a series of bioactive molecules can be functionalized with the use of readily available and removable directing groups in the presence of commercially available additives, simple ligands, and oxygen (O 2 ) as the terminal oxidant. This approach represents an economic and environmentally friendly method that could find broad applications.