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A Unified and Practical Method for Carbon–Heteroatom Cross‐Coupling using Nickel/Photo Dual Catalysis
Author(s) -
Escobar Randolph A.,
Johannes Jeffrey W.
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202000052
Subject(s) - heteroatom , nickel , aryl , chemistry , iridium , combinatorial chemistry , catalysis , coupling reaction , coupling (piping) , carbon fibers , photochemistry , organic chemistry , ring (chemistry) , computer science , materials science , alkyl , composite number , algorithm , metallurgy
Abstract While carbon–heteroatom cross‐coupling reactions have been extensively studied, many methods are specific and limited to a particular set of substrates or functional groups. Reported here is a general method that allows for C−O, C−N and C−S cross‐coupling reactions under one general set of conditions. We propose that an energy transfer pathway, in which an iridium photosensitizer produces an excited nickel(II) complex, is responsible for the key reductive elimination step that couples aryl bromides, iodides, and chlorides to 1° and 2° alcohols, amines, thiols, carbamates, and sulfonamides, and is amenable to scale up via a flow apparatus.