Work

Nickel-catalyzed C(sp2)−C(sp3) cross-coupling to access benzyl Bpins of arylboronic acids with α-halo boronic esters

Year: 2025

Type: article

Abstract: Benzyl boronic esters, as a class of organoboron compounds, are crucial intermediates in synthetic chemistry, yet the development of efficient approaches for the synthesis of these compounds remains a significant challenge. Herein, we described a nickel-catalyzed C(sp2)−C(sp3) Suzuki-type cross-coupling reaction of arylboronic acids with α-iodoboronates. The reaction offers an efficient method for synthesizing a variety of primary and secondary benzyl boronic esters. Moreover, the reaction proceeds under mild conditions and exhibits a broad substrate scope and high tolerance of functional groups. The practicality of this method has been demonstrated through gram-scale reactions and a variety of divergent transformations. Preliminary studies on enantioselective reactions have demonstrated promising stereoselectivity. Benzyl boronic esters, as a class of organoboron compounds, are crucial intermediates in synthetic chemistry, yet the development of efficient approaches for the synthesis of these compounds remains a significant challenge. Herein, the authors present a nickel-catalyzed Suzuki-type cross-coupling reaction of arylboronic acids with α-iodoboronates that efficiently synthesizes benzyl boronic esters under mild conditions, demonstrating broad substrate scope and potential for diverse applications.

Source: Communications Chemistry

DOI: 10.1038/s42004-025-01539-6

Authors: Yang Sun, Chongwei Zhu, Hui Wang

Institution: Anhui Normal University

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $3,690

Funders: National Natural Science Foundation of China, Natural Science Foundation of Anhui Province