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Electrooxidative Ruthenium‐Catalyzed C−H/O−H Annulation by Weak O ‐Coordination
Author(s) -
Qiu Youai,
Tian Cong,
Massignan Leonardo,
Rogge Torben,
Ackermann Lutz
Publication year - 2018
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.201802748
Subject(s) - ruthenium , catalysis , chemistry , electrocatalyst , electrochemistry , alkyne , annulation , metal , carboxylate , combinatorial chemistry , photochemistry , stereochemistry , organic chemistry , electrode
Electrocatalysis has been identified as a powerful strategy for organometallic catalysis, and yet electrocatalytic C−H activation is restricted to strongly N ‐coordinating directing groups. The first example of electrocatalytic C−H activation by weak O ‐coordination is presented, in which a versatile ruthenium(II) carboxylate catalyst enables electrooxidative C−H/O−H functionalization for alkyne annulations in the absence of metal oxidants; thereby exploiting sustainable electricity as the sole oxidant. Mechanistic insights provide strong support for a facile organometallic C−H ruthenation and an effective electrochemical reoxidation of the key ruthenium(0) intermediate.