52071-33-7Relevant academic research and scientific papers
Synthesis and Diversification of Macrocyclic Alkynediyl Sulfide Peptides
Godin, éric,Nguyen Thanh, Sacha,Guerrero-Morales, Javier,Santandrea, Jeffrey,Caron, Antoine,Minozzi, Clémentine,Beaucage, Noémie,Rey, Bastien,Morency, Mathieu,Abel-Snape, Xavier,Collins, Shawn K.
, p. 14575 - 14579 (2020)
The synthesis of rare macrocyclic alkynediyl sulfides by a Cu-catalyzed Csp?S cross-coupling is presented. The catalytic protocol (Cu(MeCN)4PF6/dtbbpy) promotes macrocyclization of peptides, dipeptides and tripeptides at ambient temperature (14 examples, 23→73 % yields) via thiols and bromoalkynes, and is chemoselective with regards to terminal alkynes. Importantly, the underexplored alkynediyl sulfide functionality incorporates a rigidifying structural element and opens new opportunities for diversification of macrocyclic frameworks through S oxidation, halide addition and azide–alkyne cycloaddition chemistries to integrate sulfones, halides or valuable fluorophores (7 examples, 37→92 % yields).
