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Manganese‐Catalyzed C−H Alkynylation: Expedient Peptide Synthesis and Modification
Author(s) -
Ruan Zhixiong,
Sauermann Nicolas,
Mai Elisabetta,
Ackermann Lutz
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.201611118
Subject(s) - manganese , catalysis , chemistry , combinatorial chemistry , substrate (aquarium) , aryl , halide , alkyl , silylation , alkynylation , peptide , catalytic cycle , organic chemistry , biology , biochemistry , ecology
Manganese(I)‐catalyzed C−H alkynylations with organic halides occurred with unparalleled substrate scope, and thus enabled step‐economical C−H functionalizations with silyl, aryl, alkenyl, and alkyl haloalkynes. The versatility of the manganese(I) catalysis manifold enabled C−H couplings with haloalkynes featuring, among others, fluorescent labels, steroids, and amino acids, thereby setting the stage for peptide ligation as well as the efficient molecular assembly of acyclic and cyclic peptides. A plausible catalytic cycle was proposed.