1379610-60-2Relevant academic research and scientific papers
Aluminum-Catalyzed Hydroboration of Alkenes
Bismuto, Alessandro,Cowley, Michael J.,Thomas, Stephen P.
, p. 2001 - 2005 (2018/03/13)
The aluminum-catalyzed hydroboration of alkenes with HBpin is reported using simple commercially available aluminum hydride precatalysts [LiAlH4 or sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al)]. Good substrate scope and functional group
Mechanistic studies of copper(I)-catalyzed 1,3-halogen migration
Van Hoveln, Ryan,Hudson, Brandi M.,Wedler, Henry B.,Bates, Desiree M.,Le Gros, Gabriel,Tantillo, Dean J.,Schomaker, Jennifer M.
supporting information, p. 5346 - 5354 (2015/05/13)
An ongoing challenge in modern catalysis is to identify and understand new modes of reactivity promoted by earth-abundant and inexpensive first-row transition metals. Herein, we report a mechanistic study of an unusual copper(I)-catalyzed 1,3-migration of 2-bromostyrenes that reincorporates the bromine activating group into the final product with concomitant borylation of the aryl halide bond. A combination of experimental and computational studies indicated this reaction does not involve any oxidation state changes at copper; rather, migration occurs through a series of formal sigmatropic shifts. Insight provided from these studies will be used to expand the utility of aryl copper species in synthesis and develop new ligands for enantioselective copper-catalyzed halogenation.
COPPER CATALYZED HALOGENATON AND REACTION PRODUCTS
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Paragraph 0118; 0119, (2015/01/06)
A Cu(I)-catalyzed 1,3-halogen migration reaction effectively recycles an activating group by transferring a halogen from an sp2 to a benzylic carbon with good enantioselectivity and concomitant borylation of the Ar-halo bond. The resulting enantio-enriched benzyl halide can be reacted in the same vessel under a variety of conditions to form an additional carbon-heteroatom or carbon-carbon bond while maintaining high ee. The reaction can be used to efficiently prepare novel compounds and intermediates for the preparation of therapeutics and ligands for catalysis.
Transition-metal-free synthesis of pinacol alkylboronates from tosylhydrazones
Li, Huan,Wang, Long,Zhang, Yan,Wang, Jianbo
, p. 2943 - 2946 (2012/04/18)
Highly efficient: Pinacol alkylboronates were synthesized by the reaction of tosylhydrazones with bis(pinacolato)diboron or pinacolborane under transition-metal-free conditions. This reaction represents an expeditious conversion of carbonyl functionality into a boronate group. Copyright
Copper-catalyzed recycling of halogen activating groups via 1,3-halogen migration
Grigg, R. David,Van Hoveln, Ryan,Schomaker, Jennifer M.
, p. 16131 - 16134,4 (2020/09/09)
A Cu(I)-catalyzed 1,3-halogen migration reaction effectively recycles an activating group by transferring bromine or iodine from a sp2 to a benzylic carbon with concomitant borylation of the Ar-X bond. The resulting benzyl halide can be reacted in the same vessel under a variety of conditions to form an additional carbon-heteroatom bond. Cross-over experiments using an isotopically enriched bromide source support intramolecular transfer of Br. The reaction is postulated to proceed via a Markovnikov hydrocupration of the o-halostyrene, oxidative addition of the resulting Cu(I) complex into the Ar-X bond, reductive elimination of the new sp3 C-X bond, and final borylation of an Ar-Cu(I) species to turn over the catalytic cycle.
