How to make C-N bonds using boronic acids and their derivatives without transition metals
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Publication date
2020
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Royal Society of Chemistry
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Chem. Soc. Rev., 2020,49, 5159-5177
Abstract
This tutorial review describes recent developments in carbon–nitrogen bond-forming reactions (amination, amidation, nitration and nitrosation) that involve the use of boronic acids and some of their derivatives as carbon-nucleophiles in the absence of transition-metals. Issues pertaining to reagents and
mechanisms are discussed.
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Key learning points
(1) Formation of tetrahedral boronates induces a nucleophilic activation of the carbon backbone of boronic acids and their derivatives (boronic acids, boronate
esters, or potassium organotrifluoroborates).
(2) N–B coordination of a variety of N-LG reagents (LG = Leaving Group) followed by 1,2-C(B–N)-shift triggers C–N bond formation in the absence of transitionmetals.
(3) Deoxygenation of nitro and nitroso groups turns them into useful nitrogen electrophiles for amine formation.
(4) Acylboron compounds react with N-LG reagents (LG = leaving group) through their carbonyl group to form hemiaminals that evolve to amides.