Palladium-catalyzed carboboration of alkynes using chloroborane and organozirconium reagents

Daini, Masaki; Suginome, Michinori

doi:10.1039/b809433k

Cited by 98 publications

(30 citation statements)

References 36 publications

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“…The mechanism, which was discovered by the same group, shows that oxidative addition of the B−Cl bond into the palladium complex leads to complex A with the B−Pd bond. Then internal alkyne is inserted into the B−Pd bond with high regioselectivity and (β‐borylalkenyl)chloropalladium(II) complex B is generated.…”

Section: Preparation Of Boron‐substituted 13‐dienesmentioning

confidence: 95%

“…In 2008, Suginome and Daini reported the stereoselective method to obtain ( Z , E )‐(B−Si) bifunctionalized diene 190 and 193 . The palladium‐catalyzed three‐reagent coupling engaged monochlorobis(dimethylamino)borane 187 (Scheme ; Path I) or 187 a (Scheme ; Path II), internal alkyne 188 or 191 and the bifunctionalized organozirconium compound 189 (Scheme ; Path I) or 192 (Scheme ; Path II).…”

Section: Preparation Of Boron‐substituted 13‐dienesmentioning

confidence: 99%

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Recent Advances in Boron‐Substituted 1,3‐Dienes Chemistry: Synthesis and Application

Pyziak

Walkowiak

Marciniec

2016

Chemistry A European J

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In the syntheses developed to access naturally occurring compounds, especially bioactive substances, boron-functionalized dienes (also "linchpin" reagents) are used as key reagents. Structurally unique dienes are found in nature, and play important biological and chemical roles. Recently, linchpin moieties have been proved as useful substrates for a variety of highly functionalized chemical transformations. The products of these processes are potentially of some use for the syntheses of an important class of natural products showing a wide range of biological activities. This review describes progress in the synthesis of borylsubstituted buta-1,3-dienes as well as their application in organic chemistry.

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Section: Preparation Of Boron‐substituted 13‐dienesmentioning

confidence: 95%

Section: Preparation Of Boron‐substituted 13‐dienesmentioning

confidence: 99%

Recent Advances in Boron‐Substituted 1,3‐Dienes Chemistry: Synthesis and Application

Pyziak

Walkowiak

Marciniec

2016

Chemistry A European J

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“…[28] After completion of reaction pinacol was added to replace diamine ligand in situ affording conjugated vinyl boronic esters in good yields and with high stereoselectivity for the cis -addition.…”

Section: Boryl-heckmentioning

confidence: 99%

Heck‐Like Reactions Involving Heteroatomic Electrophiles

Vulovic

Watson

2017

Eur J Org Chem

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Since the discovery of the Heck reaction in the early seventies, this reaction has become a powerful tool in synthetic organic chemistry. By employing heteroatomic instead of traditional carbon electrophiles, the Heck reaction shows an intriguing flexibility. These "hetereoatomic-Heck reactions" reinvigorate the area, offering new routes to highly useful synthetic precursors and structural motifs present in biologically active compounds. This microreview focuses on early developments leading to the heteroatomic-Heck reactions (silyl-Heck, boryl-Heck and intramolecular aza-Heck), current state of the emerging area, as well as that of a few related processes.

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“…Although Negishi reported ethylzincation [106], allylzincation [107], and methylalumination [108] with a stoichiometric amount of zirconium salt, the examples of transition-metal-catalyzed carbometalation of dialkylacetylenes were limited only to carboboration [109–110] and carbostannylation [111]. In 2005, Shirakawa and Hayashi reported iron/copper-cocatalyzed arylmagnesiation of dialkylacetylenes [112].…”

Section: Reviewmentioning

confidence: 99%

Recent advances in transition-metal-catalyzed intermolecular carbomagnesiation and carbozincation

Murakami¹,

Yorimitsu²

2013

Beilstein J. Org. Chem.

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SummaryCarbomagnesiation and carbozincation reactions are efficient and direct routes to prepare complex and stereodefined organomagnesium and organozinc reagents. However, carbon–carbon unsaturated bonds are generally unreactive toward organomagnesium and organozinc reagents. Thus, transition metals were employed to accomplish the carbometalation involving wide varieties of substrates and reagents. Recent advances of transition-metal-catalyzed carbomagnesiation and carbozincation reactions are reviewed in this article. The contents are separated into five sections: carbomagnesiation and carbozincation of (1) alkynes bearing an electron-withdrawing group; (2) alkynes bearing a directing group; (3) strained cyclopropenes; (4) unactivated alkynes or alkenes; and (5) substrates that have two carbon–carbon unsaturated bonds (allenes, dienes, enynes, or diynes).

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Palladium-catalyzed carboboration of alkynes using chloroborane and organozirconium reagents

Abstract: Three-component coupling of bis(dialkylamino)chloroborane, alkynes and organozirconium reagents proceeded in the presence of palladium catalysts, leading to the formation of stereo-defined alkenylborane derivatives via cis-carboboration of carbon-carbon triple bonds.

Cited by 98 publications

References 36 publications

Recent Advances in Boron‐Substituted 1,3‐Dienes Chemistry: Synthesis and Application

Recent Advances in Boron‐Substituted 1,3‐Dienes Chemistry: Synthesis and Application

Heck‐Like Reactions Involving Heteroatomic Electrophiles

Recent advances in transition-metal-catalyzed intermolecular carbomagnesiation and carbozincation

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