CAS 2831415-88-2, Cat. No EN300-46967412
Reagent for synthesis of α-halogenated geminal bis(boronates)
The reagent is a diborylmethane derivative used for the synthesis of α-halogenated geminal bis(boronates)1. It generates in situ halo-diborylmethyl anion that reacts with alkyl halides to form iododiborylalkanes under mild conditions2. The chloro-substituted carbanion offers improved functional group tolerance and reduced side reactions. The resulting products are versatile intermediates for Grignard, radical, and Pd-catalyzed couplings. This approach enables modular and chemoselective synthesis of valuable gem-diboron building blocks.
Synonyms: 1,3,2-dioxaborolane, 2,2′-(chloromethylene)bis[4,4,5,5-tetramethyl-; 2-[chloro(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Selected publications
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Modular Synthesis of Geminal Iododiboron Compounds via Alkylation of Chlorodiborylmethane.
Yang, Y.-F.; Ning, P.-F.; Zhang, B.; Li, M.; Xie, X.-Y.; Hong, K. Org Lett 2024, 26 (48), 10285–10290. DOI: 10.1021/acs.orglett.4c03804
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Stereoselective Access to Tetra‐ and Tri‐Substituted Fluoro‐ and Chloro‐Borylalkenes via Boron‐Wittig Reaction.
Han, S.; Lee, Y.; Jung, Y.; Cho, S. H. Angewandte Chemie International Edition 2022, 61 (41). DOI: 10.1002/anie.202210532