Efficient synthesis of alkylboronic esters via magnetically recoverable copper nanoparticle-catalyzed borylation of alkyl chlorides and bromides

Abstract

An efficient, easy to recover and reusable Cu nanocatalyst (Fe-DOPA-Cu) system has been developed for the borylation of alkyl halides, including benzyl chlorides and bromides with diboron reagents.

Synthetic Organic Transformations of Transition‐Metal Nanoparticles as Propitious Catalysts: A Review

“…Shubhankar Kumar Bose group reported the application of magnetically separable Cu nanocatalyst (FeÀ DOPAÀ Cu) for the borylation reaction of mostly primary and secondary alkyl halides 189 affording alkylboronic acid esters 191 in high yields (Scheme 79). [57] The reaction tolerated various functional groups such as esters, hemiacetals, ethers and can be operated under air in green conditions. The copper particles embedded to dopamine on nano-ferrite was synthesized and characterized by standard nano-particle characterization techniques.…”

Recyclable Copper Nanoparticles‐Catalyzed Hydroboration of Alkenes and β‐Borylation of α,β‐Unsaturated Carbonyl Compounds with Bis(Pinacolato)Diboron

“…We previously reported [19] an efficient nano‐ferrite‐supported Cu catalyst for the borylation of alkyl halides, including benzyl chlorides and bromides with alkoxy diboron reagents under mild reaction conditions [19a] . Copper is an attractive alternative to the commonly used noble metals due to its low toxicity, low environmental impact, high abundance, and low‐cost.…”

“…Copper is an attractive alternative to the commonly used noble metals due to its low toxicity, low environmental impact, high abundance, and low‐cost. Herein we describe magnetically separable Cu‐nanoparticles ( Fe‐DOPA‐Cu NPs; DOPA=dopamine) [19a,20] catalyzed regioselective hydroboration of alkenes with B 2 pin 2 under mild reaction conditions. In addition, Fe‐DOPA‐Cu NPs catalyzes the β‐borylation of α,β‐unsaturated ketones and esters to furnish alkylboronate esters, with good functional‐group compatibility.…”

Copper(I) Complex of Dihydro Bis(2‐Mercapto Benzimidazolyl) Borate as an Efficient Homogeneous Catalyst for the Synthesis of 2H‐Indazoles and 5‐Substituted 1H‐Tetrazoles

“…[31] Based on these facts, Cu-based complexes have been applied for a widespread variety of organic transformations such as cross-coupling, click chemistry, tandem and multicomponent reactions, reduction, and oxidation reactions, CÀ H functionalization, borylation, and oxidative coupling. [32][33][34][35][36][37][38][39][40][41] In recent years, literature reports in regards to enabling certain regioselective synthetic paths towards 2H-indazoles have appeared. [1,[42][43][44][45][46][47][48][49][50][51][52][53][54] A common way for the formation of highly regioselective 2H-indazoles is based on the intramolecular coupling of properly pre-functionalized substrates including 2halobenzaldehydes.…”

“…The structural diversity of copper(I) complexes provided a huge potential for the development of catalytic systems with tunable properties [31] . Based on these facts, Cu‐based complexes have been applied for a widespread variety of organic transformations such as cross‐coupling, click chemistry, tandem and multicomponent reactions, reduction, and oxidation reactions, C−H functionalization, borylation, and oxidative coupling [32–41] …”