Synthesis of 1,2-Bis- and 1,1,2-Tris-Borylalkanes under Transition Metal-Free and Solvent-Free Conditions DOI
Kiran S. Patil,

Shivakumar Reddappa,

Rakesh Kumar

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 19, 2025

Multi(boronate) esters are useful building blocks in modern chemical synthesis. Herein, we have developed an efficient, transition metal- and solvent-free method for the regioselective boration of alkenes alkynes. The alkali metal Lewis base (NaOMe)-mediated reactions, using bis(pinacolato)diboron (B2pin2) as boron reagent, resulted diboration at room temperature triboration alkynes 60 °C to produce synthetically alkyl 1,2-bis(boronate) 1,1,2-tris(boronate) esters, respectively, excellent yields with high regioselectivity. This environmentally benign protocol demonstrates a broad substrate scope good functional group tolerance gram-scale reaction further highlights practical usefulness method. proposed pathway has been evaluated based on stoichiometric reactions DFT studies.

Language: Английский

Synthesis of 1,2-Bis- and 1,1,2-Tris-Borylalkanes under Transition Metal-Free and Solvent-Free Conditions DOI
Kiran S. Patil,

Shivakumar Reddappa,

Rakesh Kumar

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 19, 2025

Multi(boronate) esters are useful building blocks in modern chemical synthesis. Herein, we have developed an efficient, transition metal- and solvent-free method for the regioselective boration of alkenes alkynes. The alkali metal Lewis base (NaOMe)-mediated reactions, using bis(pinacolato)diboron (B2pin2) as boron reagent, resulted diboration at room temperature triboration alkynes 60 °C to produce synthetically alkyl 1,2-bis(boronate) 1,1,2-tris(boronate) esters, respectively, excellent yields with high regioselectivity. This environmentally benign protocol demonstrates a broad substrate scope good functional group tolerance gram-scale reaction further highlights practical usefulness method. proposed pathway has been evaluated based on stoichiometric reactions DFT studies.

Language: Английский

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