Premium
Palladium‐Catalyzed Carbon–Fluorine and Carbon–Hydrogen Bond Alumination of Fluoroarenes and Heteroarenes
Author(s) -
Chen Wenyi,
Hooper Thomas N.,
Ng Jamues,
White Andrew J. P.,
Crimmin Mark R.
Publication year - 2017
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.201706378
Subject(s) - chemistry , palladium , catalysis , fluorine , phosphine , tandem , photochemistry , hydrogen bond , organic chemistry , molecule , materials science , composite material
Through serendipitous discovery, a palladium bis(phosphine) complex was identified as a catalyst for the selective transformation of sp 2 C−F and sp 2 C−H bonds of fluoroarenes and heteroarenes to sp 2 C−Al bonds (19 examples, 1 mol % Pd loading). The carbon–fluorine bond functionalization reaction is highly selective for the formation of organoaluminium products in preference to hydrodefluorination products (selectivity=4.4:1 to 27:1). Evidence is presented for a tandem catalytic process in which hydrodefluorination is followed by sp 2 C−H alumination.