4.6 Article

Copper catalysed protoboration of allenyl-Bdans: efficient synthesis of β-boryl allyl-Bdans

Related references

Note: Only part of the references are listed.
Article Chemistry, Multidisciplinary

Enantioselective Copper-Catalyzed sp2/sp3 Diborylation of 1-Chloro-1-Trifluoromethylalkenes

Zhenwei Fan et al.

Summary: This study reveals an enantioselective Cu-catalyzed diborylation of 1-chloro-1-trifluoromethylalkenes, leading to diborylated compounds with a gem-difluoroalkenyl moiety. Notably, the newly formed C-B bonds include a stereoselective and optically pure Csp(3)-B bond.

ACS CENTRAL SCIENCE (2022)

Article Chemistry, Organic

Regio- and stereoselective copper-catalyzed α,β-protoboration of allenoates: access to Z-β,γ-unsaturated β-boryl esters

Connor Szwetkowski et al.

Summary: A highly efficient and selective method has been developed for allenoate borylation, resulting in the synthesis of Z-beta,gamma-unsaturated beta-boryl esters. The method is performed under mild conditions and achieves high yields.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

Article Chemistry, Physical

Direct Synthesis of Multi(boronate) Esters from Alkenes and Alkynes via Hydroboration and Boration Reactions

Xianjin Wang et al.

Summary: Multi(boronate) esters have attracted increasing attention as versatile building blocks for the synthesis of complex molecules. Direct multiboration of alkenes and alkynes has been identified as an ideal route for their synthesis, with various catalytic systems developed over the past 30 years.

ACS CATALYSIS (2021)

Article Chemistry, Organic

Copper Catalyzed Protosilylation/Protoborylation of gem-Difluoroallenes

Cui-Cui Shan et al.

Summary: A new protocol has been developed for the protoborylation and protosilylation of gem-difluoroallenes, allowing for the synthesis of a variety of organoboronates and silanes. This method is efficient and versatile, applicable to both mono- and disubstituted gem-difluoroallenes. The compounds obtained can be further converted into diverse organofluorine compounds.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Regio- and Stereoselective Synthesis of Multi-Alkylated Allylic Boronates through Three-Component Coupling Reactions between Allenes, Alkyl Halides, and a Diboron Reagent

Yu Ozawa et al.

Summary: Multisubstituted allylic boronates are valuable precursors for constructing densely substituted carbon skeletons. The regio- and stereoselective coupling reactions between gem-dialkylallenes, alkyl halides, and a diboron reagent can lead to sterically congested allylic boronates. Computational study revealed that the selectivity-determining mechanism is correlated to the coordination of a boryl copper(I) species to the allene substrate as well as the borylcupration step.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Multidisciplinary

Copper(ii)-catalyzed protoboration of allenes in aqueous media and open air

Russell F. Snead et al.

Summary: A method has been developed for the facile Cu(ii)-catalyzed protoboration of monosubstituted allenes in aqueous media under atmospheric conditions, with good yields and site selectivity.

NEW JOURNAL OF CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Sterically congested boronate and silane synthesis via electronically controlled protoboration and protosilylation

Cheng-Qiang Wang et al.

Summary: Copper-catalyzed protoboration/silylation of gem-difluoroallenes shows abnormal reactivity and regioselectivity, with fluorine substituents critical for high fidelity transformations. This methodology is applied to late-stage modification of natural product-derived compounds and highlights the utility of gem-difluoroalkenes in further synthetic elaborations.

CELL REPORTS PHYSICAL SCIENCE (2021)

Article Chemistry, Organic

Regio-divergent hydroboration of terminal allenes controlled by nickel and cobalt catalysts†

Ying Yang et al.

Summary: A highly efficient and regioselective method for allene hydroboration has been developed, with the regioselectivity primarily controlled by the choice of metal used. Nickel and cobalt catalysts were found to give complementary regioselectivity when employing easily accessible phosphorus ligands. This study marks the first reported use of nickel catalyst in allene hydroboration reactions.

ORGANIC CHEMISTRY FRONTIERS (2021)

Review Chemistry, Multidisciplinary

Advances in transition metal-free deborylative transformations of gem-diborylalkanes

Woohyun Jo et al.

Summary: This feature article summarises recent progress in the synthetic utilisation of alpha-borylcarbanions, including carbon-carbon bond formation with alkyl halides, alkenes, N-heteroarenes, and carbonyls. Carbon-boron bond formation in organohalides mediated by alpha-borylcarbanions is also summarised.

CHEMICAL COMMUNICATIONS (2021)

Article Chemistry, Organic

Copper-catalyzed boroacylation of allenes to access tetrasubstituted vinylboronates

Bing-Xue Shen et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2020)

Article Chemistry, Organic

Cu-Catalyzed Silylation and Borylation of Vinylidene Cyclopropanes

Jichao Chen et al.

ORGANIC LETTERS (2019)

Article Chemistry, Multidisciplinary

Synthesis of γ-Boryl-Substituted Homoallylic Alcohols with anti Stereochemistry Based on a Double-Bond Transposition

Tomoya Miura et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Physical

Regioselective Diboration and Silaboration of Allenes Catalyzed by Au Nanoparticles

Marios Kidonakis et al.

ACS CATALYSIS (2018)

Article Chemistry, Multidisciplinary

Enantioselective palladium-catalyzed diboration of 1,1-disubstituted allenes

Jiawang Liu et al.

CHEMICAL SCIENCE (2017)

Review Chemistry, Multidisciplinary

Enantioselective copper catalysed, direct functionalisation of allenes via allyl copper intermediates

Alexander P. Pulis et al.

CHEMICAL SCIENCE (2017)

Article Chemistry, Organic

Copper-catalyzed highly selective approach to 2-boroallylic silanes from allenylsilanes

Liu Song et al.

ORGANIC CHEMISTRY FRONTIERS (2017)

Article Chemistry, Multidisciplinary

Stereoselective Traceless Borylation-Allenation of Propargylic Epoxides: Dual Role of the Copper Catalyst

Carlos Jarava-Barrera et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

Article Chemistry, Multidisciplinary

Copper-Catalyzed Borylcupration of Allenylsilanes

Weiming Yuan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Cascade Copper-Catalyzed 1,2,3-Trifunctionalization of Terminal Allenes

Wanxiang Zhao et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

Copper-Catalyzed Borylation of α-Alkoxy Allenes with Bis(pinacolato)diboron: Efficient Synthesis of 2-Boryl 1,3-Butadienes

Kazuhiko Semba et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Article Chemistry, Multidisciplinary

Amide-Controlled Highly Selective Catalytic Borylcupration of Allenes

Weiming Yuan et al.

CHEMISTRY-A EUROPEAN JOURNAL (2013)

Article Chemistry, Multidisciplinary

Highly Selective Copper-Catalyzed Hydroboration of Allenes and 1,3-Dienes

Kazuhiko Semba et al.

CHEMISTRY-A EUROPEAN JOURNAL (2013)

Article Chemistry, Applied

Ligand Controlled Highly Selective Copper-Catalyzed Borylcuprations of Allenes with Bis(pinacolato)diboron

Weiming Yuan et al.

ADVANCED SYNTHESIS & CATALYSIS (2012)

Review Chemistry, Physical

Catalytic, Direct Synthesis of Bis(boronate) Compounds

Jun Takaya et al.

ACS CATALYSIS (2012)

Article Chemistry, Multidisciplinary

(E)- and (Z)-ss-Borylallylsilanes by Alkyne Silaboration Followed by Regio- and Stereoselective Double-Bond Migration

Toshimichi Ohmura et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

Article Chemistry, Multidisciplinary

Transition-Metal-Free Diboration Reaction by Activation of Diboron Compounds with Simple Lewis Bases

Amadeu Bonet et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

Article Chemistry, Multidisciplinary

Regio- and stereoselective copper-catalyzed beta-borylation of allenoates by a preactivated diboron

Steven B. Thorpe et al.

CHEMICAL COMMUNICATIONS (2011)

Article Chemistry, Multidisciplinary

Development, mechanism, and scope of the palladium-catalyzed enantioselective allene diboration

Heather E. Burks et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

Article Chemistry, Multidisciplinary

Sequential Pd-catalyzed asymmetric allene diboration/α-aminoallylation

JD Sieber et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

Article Chemistry, Multidisciplinary

Efficient homogeneous catalysis in the reduction of CO2 to CO

DS Laitar et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)

Article Chemistry, Organic

Concatenated catalytic asymmetric allene diboration/allylation/functionalization

AR Woodward et al.

ORGANIC LETTERS (2005)

Article Chemistry, Multidisciplinary

Palladium-catalyzed enantioselective diboration of prochiral allenes

NF Pelz et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2004)

Article Chemistry, Multidisciplinary

Unusual diboration of allenes catalyzed by palladium complexes and organic iodides: A new efficient route to biboronic compounds

FY Yang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2001)