Site-selective and diastereoselective functionalization of α-amino acid and peptide derivatives via palladium-catalyzed sp³ C–H activation

Abstract

α-Amino acid and peptide derivatives are important in synthetic organic chemistry and medicinal chemistry, which attract many chemists to develop new methods for synthesis of them. Palladium-catalyzed sp3 C-H activation/functionalization...

Cobalt-Catalyzed C(sp2)–H Carbonylation of Amino Acids Using Picolinamide as a Traceless Directing Group

“…Amino acids and peptides play an essential role in medicinal chemistry, synthetic organic chemistry, and biotechnology; therefore, direct functionalization of amino acid derivatives and peptides via C–H bond activation has attracted immense interest during the past decade . In addition, the late-stage modification of peptides has a tremendous potential to promote the development of innovative peptide drugs .…”

“…In addition, the late-stage modification of peptides has a tremendous potential to promote the development of innovative peptide drugs . Progress on direct C–H bond functionalization of amino acid derivatives has been achieved mainly using late transition metal catalysis . The functionalization of amino acid C­(sp 3 )–H bonds is relatively well-developed allowing installation of various functional groups both in the α-position and on the amino acid side chain .…”

Metal‐Catalyzed C(sp2)−H Functionalization Processes of Phenylalanine‐ and Tyrosine‐Containing Peptides

“…One of the most exploited metal‐catalyzed tagging techniques within a peptide sequence involves the Pd‐catalyzed C−H arylation reaction with aryl halides through a Pd(II)/Pd(IV) regime. The latter has been described to site‐selectively occur both at the C2 site of indoles within Trp‐containing peptides [9] and at the C(sp 3 )−H of aliphatic side‐chains [8b,c] of Ala, Val or even Phe residues [13] . However, the analogous process occurring at the δ‐C(sp 2 )−H bonds within the phenyl ring of Phe or Tyr units has been comparatively unexplored.…”

Recent advances in catalytic oxidative reactions of phenols and naphthalenols

“…(d) Oxidative cyclization of phenols via C(sp 2 )-H functionalization Catalytic C-H bond functionalization for C-C bond formation has attracted tremendous interest from the synthetic community with high potential to replace classical catalytic cross-coupling reactions involving a stoichiometric amount of one or two organometallic species. [125][126][127][128][129][130][131][132] Therefore, it is highly appealing to investigate C-H functionalization of arenols. We aim to show the examples of direct C(sp 2 )-H functionalization reactions that preserve aromaticity, focusing on the most recent examples of phenol oxidative cyclization via C(sp 2 )-H functionalization, since Porco has provided comprehensive assessments in the field of oxidative phenolic dearomatization.…”