Work

Mild Generation of Highly Nucleophilic N ‐Heterocyclic Carbene Boryl Anion From Neutral sp 2 –sp 3 Diboron Reagents and Its Applications in Nucleophilic Borylation

Year: 2026

Type: article

Abstract: ABSTRACT Due to its high activity, the synthesis or generation of the N ‐heterocyclic carbene (NHC) boryl anion remains challenging, with only limited methods available. Traditional stabilization through bulky ligands or aromatic systems restricts its reactivity as a boron synthon. In this work, we present a straightforward strategy for the in situ generation of an NHC boryl anion at room temperature through the reaction of neutral sp 2 –sp 3 diboron reagent (NHC)BH 2 Bpin with KO t Bu. This less sterically hindered and strongly nucleophilic boryl anion demonstrates broad reactivity with diverse electrophiles, including those that are unreactive with other types of boryl anions or traditional diboron reagents. These nucleophilic borylation reactions enable the synthesis of a diverse array of four‐coordinate organoboron compounds. Detailed mechanistic studies and DFT calculations confirm the intermediacy of the NHC boryl anion and provide clear insights into the reaction pathways for the newly discovered reactivities.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.7517492

Authors: Weixuan Sun, Peiqi Zhang, Hairong Lyu

Institutions: Chinese University of Hong Kong, Hong Kong University of Science and Technology

Language: English

Topic: Organoboron and organosilicon chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,510

Funders: Croucher Foundation, Chinese University of Hong Kong, Hong Kong University of Science and Technology