title: Making Dimethylamino a Transformable Directing Group by Nickel-Catalyzed C-N Borylation.
abstract: The dimethylamino (Me2N) 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 Me2N-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 C-N borylations of aryl- and benzyl-dimethylamines that permit the conversion of a huge library of largely underutilized Me2N-containing organic molecules into various functional molecules by taking advantage of the wealth of existing C-B functionalization methods.
authors.affiliation: Institute of Transformative Bio-Molecules (WPI-ITbM) and, Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602 (Japan).
authors.forename: Hua
authors.initials: H
authors.lastname: Zhang
authors.affiliation: Institute of Transformative Bio-Molecules (WPI-ITbM) and, Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602 (Japan).
authors.forename: Shinya
authors.initials: S
authors.lastname: Hagihara
authors.affiliation: Institute of Transformative Bio-Molecules (WPI-ITbM) and, Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602 (Japan). itami@chem.nagoya-u.ac.jp.|JST-ERATO, Itami Molecular Nanocarbon Project, Nagoya University, Chikusa, Nagoya 464-8602 (Japan). itami@chem.nagoya-u.ac.jp.
authors.forename: Kenichiro
authors.initials: K
authors.lastname: Itami
keywords: CN borylation; catalysis; dimethylamino group; directing group; nickel