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Metal‐Free Direct Transformation of Aryl Boronic Acid to Primary Amines

Puneet Kumar, Saumya Verma, Komal Rathi, Dinesh Chandra, Ved Prakash Verma, Jawahar L. Jat

2022European Journal of Organic Chemistry14 citationsDOI

Abstract

Abstract In this work, we report a transition‐metal free approach for the construction of primary aromatic amines from aryl boronic acids and esters with N ‐Boc‐ O ‐tosylhydroxylamine as an amine surrogate. Bench stable TsONHBoc is easy to use and it produces a non‐interfering water‐soluble by‐product. The protocol is operative for both electron‐rich and electron‐deficient aryl boronic acids under acidic conditions, where the former arenes affords a better yield of the desired product. Even, sterically hindered and halogenated substrates are easily amenable under this reaction condition. The current protocol can be scaled up to produce gram‐scale primary aromatic amines.

Topics & Concepts

ChemistryArylSteric effectsAmine gas treatingBoronic acidPrimary (astronomy)Yield (engineering)Combinatorial chemistryOrganic chemistryAromatic amineAlkylMaterials sciencePhysicsAstronomyMetallurgyCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsOrganoboron and organosilicon chemistry
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