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Making Dimethylamino a Transformable Directing Group by Nickel‐Catalyzed CN Borylation
Author(s) -
Zhang Hua,
Hagihara Shinya,
Itami Kenichiro
Publication year - 2015
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.201503596
Subject(s) - borylation , catalysis , aryl , combinatorial chemistry , functional group , chemistry , organic molecules , nickel , surface modification , group (periodic table) , molecule , organic synthesis , small molecule , stereochemistry , organic chemistry , alkyl , polymer , biochemistry
The dimethylamino (Me 2 N) group is arguably the most versatile functional group capable of highly efficient and site‐selective directed aromatic functionalizations at the ortho ‐, meta ‐, and para ‐positions depending on reaction conditions. While the repertoire of Me 2 N‐directed reactions is growing at a rapid pace, the lack of a general method to transform this group to other functionalities hampers its wider application in organic synthesis. Here we report nickel‐catalyzed CN borylations of aryl‐ and benzyl‐dimethylamines that permit the conversion of a huge library of largely underutilized Me 2 N‐containing organic molecules into various functional molecules by taking advantage of the wealth of existing CB functionalization methods.