Boroalkyl Group Migration Provides a Versatile Entry into α-Aminoboronic Acid Derivatives

A reaction exemplifying migration of boron-substituted carbon is described. We show that α-boroalkyl groups of transient boroalkyl acyl azide intermediates readily migrate from carbon to nitrogen. This process allows access to a new class of stable molecules, α-boryl isocyanates, from α-borylcarboxylic acid precursors. The methodology facilitates synthesis of a wide range of α-aminoboronic acid derivatives, including α,α-disubstituted analogues

Condensation-Driven Assembly of Boron-Containing Bis(Heteroaryl) Motifs Using a Linchpin Approach

Herein, we describe the bromomethyl acyl boronate linchpin–an enabling reagent for the condensation-driven assembly of novel bis­(heteroaryl) motifs. This building block is readily accessible from commercially available starting materials. A variety of 2-amino- and 2-methylpyridines were reacted with MIDA-protected bromomethyl acylboronate to afford 2-boryl imidazo­[1,2-<i>a</i>]­pyridine and 2-boryl indolizine derivatives, respectively, in excellent yields. Subsequent condensation with hydroxyamidines and hydrazonamides converted the intermediate heterocycles into novel boron-containing bis­(heteroaryl) units characterized by high thermal stability

Condensation-Driven Assembly of Boron-Containing Bis(Heteroaryl) Motifs Using a Linchpin Approach

Herein, we describe the bromomethyl acyl boronate linchpin–an enabling reagent for the condensation-driven assembly of novel bis­(heteroaryl) motifs. This building block is readily accessible from commercially available starting materials. A variety of 2-amino- and 2-methylpyridines were reacted with MIDA-protected bromomethyl acylboronate to afford 2-boryl imidazo­[1,2-<i>a</i>]­pyridine and 2-boryl indolizine derivatives, respectively, in excellent yields. Subsequent condensation with hydroxyamidines and hydrazonamides converted the intermediate heterocycles into novel boron-containing bis­(heteroaryl) units characterized by high thermal stability

Condensation-Driven Assembly of Boron-Containing Bis(Heteroaryl) Motifs Using a Linchpin Approach

Herein, we describe the bromomethyl acyl boronate linchpin–an enabling reagent for the condensation-driven assembly of novel bis­(heteroaryl) motifs. This building block is readily accessible from commercially available starting materials. A variety of 2-amino- and 2-methylpyridines were reacted with MIDA-protected bromomethyl acylboronate to afford 2-boryl imidazo­[1,2-<i>a</i>]­pyridine and 2-boryl indolizine derivatives, respectively, in excellent yields. Subsequent condensation with hydroxyamidines and hydrazonamides converted the intermediate heterocycles into novel boron-containing bis­(heteroaryl) units characterized by high thermal stability