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A Carbene‐Extended ATRA Reaction
Author(s) -
Wu Guojiao,
Börger Jennifer,
Jacobi von Wangelin Axel
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201909872
Subject(s) - carbenoid , bifunctional , carbene , chemistry , atom economy , alkyne , reactivity (psychology) , combinatorial chemistry , organic synthesis , adduct , atom transfer radical polymerization , catalysis , computational chemistry , organic chemistry , rhodium , medicine , polymer , alternative medicine , pathology , copolymer
Atom‐transfer radical addition (ATRA) reactions have gained a strong foothold in organic synthesis by virtue of their operational simplicity, synthetic versatility, and perfect atom economy. A rich chemical space can be accessed through clever combinations of the simple starting materials. Many variations of this general motif have been reported. However, the vast majority involve the addition of an organic halide across a C=C double bond, resulting in the formation of 1,2‐bifunctional products. This report introduces a significant expansion of this general reactivity concept to give 1,3‐bifunctional adducts through the combination of 1,1‐ATRA to a carbenoid and 1,2‐ATRA to an alkyne. Both processes operate under mild conditions (RT, 5 h) with the same commercial catalyst (CoBr 2 , dppbz).