4.7 Article

A stable silylborane with diminished boron Lewis acidity

Related references

Note: Only part of the references are listed.
Review Chemistry, Applied

Synthetic Chemistry with Lewis Acidity-Diminished B(aam) and B(dan) Groups: Borylation Reactions and Direct Cross-Couplings

Shintaro Kamio et al.

Summary: Recent advances in the synthesis of organoboron compounds with diminished boron Lewis acidity via B(aam)- and B(dan)-installing borylation reactions have attracted growing attention due to their unique reactivity and outstanding stability toward air and moisture. Direct Suzuki-Miyaura cross-couplings with previously believed unreactive R-B(aam)/B(dan) compounds have also been discussed.

ADVANCED SYNTHESIS & CATALYSIS (2021)

Article Chemistry, Physical

Origins of Internal Regioselectivity in Copper-Catalyzed Borylation of Terminal Alkynes

Takumi Tsushima et al.

Summary: The highly internal-selective borylation of terminal alkynes under copper catalysis was achieved by diminishing boron-Lewis acidity and introducing ligand-derived steric bulk around a copper center. The use of an anthranilamide-substituted boron moiety enabled internal regioselectivity and Suzuki-Miyaura cross-coupling activity to be compatibly achieved, providing a direct and universal approach to variously substituted branched alkenylboron compounds.

ACS CATALYSIS (2021)

Article Chemistry, Multidisciplinary

Copper-Catalyzed Synthesis of Tetrasubstituted Alkenes via Regio- and anti-Selective Addition of Silylboronates to Internal Alkynes

Hirokazu Moniwa et al.

Summary: A new and complementary method using copper-catalyzed regio- and anti-selective addition of silylboronates to unsymmetric internal alkynes has been developed for the synthesis of structurally defined tetrasubstituted alkenes. Various unactivated alkynes can be employed with high selectivity under simple and mild conditions, allowing further functionalization of the alkene products utilizing silyl and boryl groups.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Article Chemistry, Multidisciplinary

Borylation and Stannylation Reactions with Tuning of Lewis Acidity

Hiroto Yoshida

Summary: In this study, a B(dan) moiety of diminished boron-Lewis acidity was efficiently installed into organic frameworks through copper catalyzed three-component carboboration of alkenes. The resulting dan-substituted organoboranes were obtained via borylative substitution of carbon electrophiles. Additionally, synthesis of diverse organostannanes based upon copper-catalyzed carbostannylation and borylstannylation have been described, where the Lewis acidity increment of a tin center facilitated the progress in some cases.

CHEMICAL RECORD (2021)

Article Chemistry, Organic

MICROWAVE-ASSISTED SYNTHESIS OF 2-AMINOTHIOPHENE DERIVATIVES VIA IMPROVED GEWALD REACTIONS

Bankang Ruan et al.

Summary: A new and efficient method was developed in this study to prepare 2-aminothiophene derivatives through an improved Gewald reaction. Thirty-one final products were successfully synthesized under microwave radiation with isolated yields ranging from 57% to 95%. These products can serve as building blocks in drug discovery.

HETEROCYCLES (2021)

Article Chemistry, Multidisciplinary

Copper-catalyzed regioselective trans-silaboration of internal arylalkynes with stereochemical switch to cis-addition mode

Toshimichi Ohmura et al.

Summary: The copper-catalyzed silafunctionalization of alkynes using silylboronic ester as a silicon source has made rapid progress. The trans-selective 1,2-addition of silylboronic esters to internal arylalkynes was efficiently promoted by the CuOt-Bu/RCy2P/NaOt-Bu catalysts, with a stereochemical switch to cis-addition observed in reactions utilizing Me-2(i-PrO)Si-B(pin) in hydrocarbon solvents including cyclohexane.

CHEMICAL COMMUNICATIONS (2021)

Review Chemistry, Multidisciplinary

Activation of the Si-B interelement bond related to catalysis

Jian-Jun Feng et al.

Summary: Si-B reagents, including silylboronic esters and silylboranes, have gained attention for their versatility in introducing silicon and boron atoms into organic frameworks. Recent advancements in the field have led to diverse transformations through transition-metal-catalysed or transition-metal-free Si-B bond activation. This review focuses on the new applications of Si-B reagents and also discusses new methods of their preparation and relevant reaction mechanisms.

CHEMICAL SOCIETY REVIEWS (2021)

Article Chemistry, Multidisciplinary

Silaboration of [1.1.1]Propellane: A Storable Feedstock for Bicyclo[1.1.1]pentane Derivatives

Masaki Kondo et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

General Synthesis of Trialkyl- and Dialkylarylsilylboranes: Versatile Silicon Nucleophiles in Organic Synthesis

Ryosuke Shishido et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Organic

Pyridine-Based Organocatalysts for Regioselective syn-1,2-Silaboration of Terminal Alkynes and Allenes

Yohei Morimasa et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2019)

Article Chemistry, Multidisciplinary

Anthranilamide (aam)-substituted arylboranes in direct carbon-carbon bond-forming reactions

Shintaro Kamio et al.

CHEMICAL COMMUNICATIONS (2019)

Article Chemistry, Multidisciplinary

Anthranilamide (aam)-substituted diboron: palladium-catalyzed selective B(aam) transfer

Shintaro Kamio et al.

CHEMICAL COMMUNICATIONS (2018)

Article Chemistry, Multidisciplinary

N,B-Bidentate Boryl Ligand-Supported Iridium Catalyst for Efficient Functional-Group-Directed C-H Borylation

Guanghui Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Organic

Copper-catalyzed direct borylation of alkyl, alkenyl and aryl halides with B(dan)

Hiroto Yoshida et al.

ORGANIC CHEMISTRY FRONTIERS (2017)

Review Chemistry, Multidisciplinary

Activation of the Si-B Interelement Bond: Mechanism, Catalysis, and Synthesis

Martin Oestreich et al.

CHEMICAL REVIEWS (2013)

Article Chemistry, Multidisciplinary

Switch of Regioselectivity in Palladium-Catalyzed Silaboration of Terminal Alkynes by Ligand-Dependent Control of Reductive Elimination

Toshimichi Ohmura et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Article Chemistry, Inorganic & Nuclear

Convenient preparation of silylboranes

M Suginome et al.

ORGANOMETALLICS (2000)

Article Chemistry, Inorganic & Nuclear

Synthesis of (boryl)(silyl)iminomethanes by insertion of isonitriles into silicon-boron bonds

M Suginome et al.

ORGANOMETALLICS (2000)