AI Article Synopsis
- Cyclopropane compounds are important in organic synthesis and pharmaceuticals, leading to the development of a new reagent called CHI(Bpin) for creating cyclopropylboronates from alkenes.
- This reagent can be easily produced in large quantities from common starting materials and allows for efficient synthesis with high selectivity and compatibility with various functional groups.
- The process uses a mechanism involving radical reactions and is facilitated by a photocatalyst under visible light, enabling the modification of complex molecules at later stages.
Article Abstract
Cyclopropane skeletons play a prominent role in the development of organic synthesis and pharmaceutical chemistry. Herein, we report the design and synthesis of a stable, multifunctional (diborylmethyl)iodide reagent (CHI(Bpin) ) for the photoinduced cyclopropanation of alkenes, providing an array of 1,2-substituted cyclopropylboronates in good yields. This α-haloboronic ester can be readily synthesized on a multigram scale from commercially available starting materials. Furthermore, the protocol displays high chemo- and diastereoselectivity, excellent functional-group tolerance, and allows for late-stage borylcyclopropanation of complex molecules. Mechanistic studies reveal that the borylcyclopropanation proceeds through a radical addition/polar cyclization pathway mediated by the photocatalyst fac-Ir(ppy) and visible light.
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| http://dx.doi.org/10.1002/anie.202305175 | DOI Listing |
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