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Direct C−H Phosphonylation of Electron‐Rich Arenes and Heteroarenes by Visible‐Light Photoredox Catalysis
Author(s) -
Shaikh Rizwan S.,
Ghosh Indrajit,
König Burkhard
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201701283
Subject(s) - photoredox catalysis , catalysis , chemistry , aryl , combinatorial chemistry , ammonium persulfate , photochemistry , photocatalysis , molecule , persulfate , functional group , atom economy , visible spectrum , organic chemistry , materials science , polymer , alkyl , optoelectronics , polymerization
The direct transformation of ubiquitous, but chemically inert C−H bonds into diverse functional groups is an important strategy in organic synthesis that improves the atom economy and faclitates the preparation and modification of complex molecules. In contrast to the wide applications of aryl phosphonates, their synthesis via direct C−H bond phosphonylation is a less explored area. We report here a general, mild, and broadly applicable visible‐light photoredox C−H bond phosphonylation method for electron‐rich arenes and heteroarenes. The photoredox catalytic protocol utilizes electron‐rich arenes and biologically important heteroarenes as substrates, [Ru(bpz) 3 ][PF 6 ] 2 as photocatalyst, ammonium persulfate as oxidant, and trialkyl phosphites as the phosphorus source to provide a wide range of aryl phosphonates at ambient temperature under very mild reaction conditions.