Year: 2024
Type: article
Abstract: Cyclopropanes are among the most important structural units in natural products, pharmaceuticals, and agrochemicals. Herein, we report a manganese-catalyzed cyclopropanation of allylic alcohols with sulfones as carbene alternative precursors via a borrowing hydrogen strategy under mild conditions. Various allylic alcohols and arylmethyl trifluoromethyl sulfones work efficiently in this borrowing hydrogen transformation and thereby deliver the corresponding cyclopropylmethanol products in 58% to 99% yields. Importantly, a major benefit of this transformation is that the versatile free alcohol moiety is retained in the resultant products, which can undergo a wide range of downstream transformations to provide access to a series of functional molecules. Mechanistic studies support a sequential reaction mechanism that involves catalytic dehydrogenation, Michael addition, cyclization, and catalytic hydrogenation. Developing readily available and bench-stable reagents for the cyclopropanation of olefins is needed as traditional methodologies mainly rely on carbene-based strategies. Herein, the authors report a manganese-catalyzed cyclopropanation of allylic alcohols with sulfones via a borrowing hydrogen strategy under mild conditions.
Source: Nature Communications
Authors: Ke Yu, Qin Nie, Qianjin Chen, Weiping Liu
Institution: Donghua University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: gold
Estimated APC paid: $6,790
Awards: G255903850, G4200319469
OpenAlex ID: W4401464699