Palladium‐Catalyzed Carbon–Fluorine and Carbon–Hydrogen Bond Alumination of Fluoroarenes and Heteroarenes | Zendy

Chen Wenyi | Zendy; Hooper Thomas N. | Zendy; Ng Jamues | Zendy; White Andrew J. P. | Zendy; Crimmin Mark R. | Zendy

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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.

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