Copper-catalyzed hydroboration of propargyl-functionalized alkynes in water

Costa, Jessie Sobieski da; Braun, Roger Kainan; Horn, Pedro A.; Lüdtke, Diogo S.; Moro, Angélica V.

doi:10.1039/c6ra14465a

Cited by 28 publications

(18 citation statements)

References 55 publications

(13 reference statements)

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“…57 Building on earlier reports of enone borylation described by Santos and others (vide infra), 58,59 there have been reports of alkyne hydroboration under aqueous conditions in which hydroxide rather than alkoxide bases can be used (Scheme 13). 60,61 3.1.2 Carboboration. Greater structural complexity is possible when the intermediate organoboryl copper complex is intercepted by alternative electrophiles.…”

Section: Reactions Of Copper-boryl Species With C-c Multiple Bondsmentioning

confidence: 99%

Copper-boryl mediated organic synthesis

et al. 2018

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Organoboron compounds are valuable synthetic intermediates that find application in a diverse variety of processes including both C-X and C-C bond-forming transformations. This has been achieved by using a variety of boron derivatives. Of these, boronate esters are probably the most versatile and, reflecting this, methods for the generation of boronate esters are of considerable current interest. Given the mild reaction conditions, good functional group tolerance, and low cost of the metal catalyst, the use of copper-boryl reagents is particularly attractive. In this review, methodologies in copper-boryl chemistry are discussed and the many different transformations possible are surveyed.

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Section: Reactions Of Copper-boryl Species With C-c Multiple Bondsmentioning

confidence: 99%

Copper-boryl mediated organic synthesis

et al. 2018

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“…For some time now, catalytic versions of the copper‐mediated borylation of alkynes, using (Bpin) 2 as boryl donor, have been developed . Remarkably, inversions of regioselectivities have been observed, particularly by introducing different copper ligands . For aryl‐substituted terminal alkynes, and with non‐bulky ligands, the selectivity is generally in favor of the linear adduct (or β‐product, Table ) .…”

Section: Figurementioning

confidence: 99%

Cyclodextrin Cavity‐Induced Mechanistic Switch in Copper‐Catalyzed Hydroboration

et al. 2017

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N-heterocyclic carbene-capped cyclodextrin (ICyD) ligands, α-ICyD and β-ICyD derived from α- and β-cyclodextrin, respectively give opposite regioselectivities in a copper-catalyzed hydroboration. The site-selectivity results from two different mechanisms: the conventional parallel one and a new orthogonal mechanism. The shape of the cavity was shown not only to induce a regioselectivity switch but also a mechanistic switch. The scope of interest of the encapsulation of a reactive center is therefore broadened by this study.

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“…[111] In this line, Moro Group developed β-regioselective hydroboration of propargylic functionalized alkynes using Cu(OAc) 2 -dppe (L24) under micellar catalysis in aqueous medium in presence of cheaper hydroxide base (Scheme 12c). [112] In 2016, Yun Group reported a stereodivergent synthesis of vinylboronates through Cu(I)-catalyzed hydroboration of terminal aryl acetylenes with HBdan to access β-alkenylboronates which are stereocomplemenraty to each other (Scheme 13a). [113] The (SIPr)-CuCl/NaOt-Bu combination produced (E)-β-alkenylboronates, whereas the copper-carboxylates coordinated with a phosphine ligand (DPEphos-CuTC) generated the β-alkenylboronates with excellent Z-stereoselectivity via trans-addition of the HBdan to terminal acetylenes.…”

Section: Terminal Alkynes and Enynesmentioning

confidence: 99%

Copper‐Catalyzed Preparation of Alkenylboronates and Arylboronates

et al. 2021

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Organoboron compounds, especially alkenylboronates and arylboronates are highly useful reagents and versatile building blocks in the modern synthetic chemistry toolbox. This review focuses on copper-catalyzed routes to access alkenyl-and arylboronate esters. Various copper salts and ligands have been employed to access them in excellent regio-and stereoselectivity as well as high yields. Both addition and substitution reactions to alkenylboronates have been highlighted based on various methodologies including hydroboration, carboboration, borylative opening of propargyl three-and four-membered rings, dehalogenative borylation of alkenyl bromides and iodides, defluoroborylation of fluoroalkenes and direct C(sp 2 )À H bond activation of alkenes. Preparation of arylboronates involving borylation of aryl halides, C(sp 2 )À H borylation of arenes and cascade 1,3-halogen migration/borylation of 2halostyrenes have been reviewed. Mechanistic aspects of those borylation reactions are discussed briefly.

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Copper-catalyzed hydroboration of propargyl-functionalized alkynes in water

Abstract: The Cu-catalyzed hydroboration of alkynes in operationally simple and environmentally friendly conditions is reported.

Cited by 28 publications

References 55 publications

Copper-boryl mediated organic synthesis

Copper-boryl mediated organic synthesis

Cyclodextrin Cavity‐Induced Mechanistic Switch in Copper‐Catalyzed Hydroboration

Copper‐Catalyzed Preparation of Alkenylboronates and Arylboronates

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