4.8 Article

Manganese-Catalyzed C-H Alkynylation: Expedient Peptide Synthesis and Modification

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 12, Pages 3172-3176

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201611118

Keywords

alkynes; C-H activation; manganese; peptides; reaction mechanisms

Funding

  1. European Research Council under the European Community's Seventh Framework Program (FP7 )/ERC [307535]
  2. CSC
  3. CaSuS

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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.

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