Issue 3, 2024

Catalytic acceptorless dehydrogenative borylation of styrenes enabled by a molecularly defined manganese complex

Abstract

In this study, we employed a 3d metal complex as a catalyst to synthesize alkenyl boronate esters through the dehydrogenative coupling of styrenes and pinacolborane. The process generates hydrogen gas as the sole byproduct without requiring an acceptor, rendering it environmentally friendly and atom-efficient. This methodology demonstrated exceptional selectivity for dehydrogenative borylation over direct hydroboration. Additionally, it exhibited a preference for borylating aromatic alkenes over aliphatic ones. Notably, derivatives of natural products and bioactive molecules successfully underwent diversification using this approach. The alkenyl boronate esters served as precursors for the synthesis of various pharmaceuticals and potential anticancer agents. Our research involved comprehensive experimental and computational studies to elucidate the reaction pathway, highlighting the B–H bond cleavage as the rate-determining step. The catalyst's success was attributed to the hemilability and metal–ligand bifunctionality of the ligand backbone.

Graphical abstract: Catalytic acceptorless dehydrogenative borylation of styrenes enabled by a molecularly defined manganese complex

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Article information

Article type
Edge Article
Submitted
17 Oct 2023
Accepted
09 Dec 2023
First published
11 Dec 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2024,15, 1098-1105

Catalytic acceptorless dehydrogenative borylation of styrenes enabled by a molecularly defined manganese complex

K. Das, A. Kundu, K. Sarkar, D. Adhikari and B. Maji, Chem. Sci., 2024, 15, 1098 DOI: 10.1039/D3SC05523J

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