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Photochemical Dual‐Catalytic Synthesis of Alkynyl Sulfides
Author(s) -
Santandrea Jeffrey,
Minozzi Clémentine,
Cruché Corentin,
Collins Shawn K.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201705903
Subject(s) - chemistry , catalysis , carbazole , sulfide , photocatalysis , combinatorial chemistry , photochemistry , steric effects , functional group , organic synthesis , sulfur , continuous flow , organic chemistry , physics , mechanics , polymer
A photochemical dual‐catalytic cross‐coupling to form alkynyl sulfides via C(sp)−S bond formation is described. The cross‐coupling of thiols and bromoalkynes is promoted by a soluble organic carbazole‐based photocatalyst using continuous flow techniques. Synthesis of alkynyl sulfides bearing a wide range of electronically and sterically diverse aromatic alkynes and thiols can be achieved in good to excellent yields (50–96 %). The simple continuous flow setup also allows for short reaction times (30 min) and high reproducibility on gram scale. In addition, we report the first application of photoredox/nickel dual catalysis towards macrocyclization, as well as the first example of the incorporation of an alkynyl sulfide functional group into a macrocyclic scaffold.