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Literature DB >> 20698667

Chemoselective and regiospecific Suzuki coupling on a multisubstituted sp(3)-carbon in 1,1-diborylalkanes at room temperature.

Kohei Endo¹, Takahiro Ohkubo, Munenao Hirokami, Takanori Shibata.

Abstract

The palladium-catalyzed Suzuki-Miyaura cross-coupling on a multisubstituted sp(3)-carbon in 1,1-diborylalkanes was achieved at room temperature. The generation of a monoborate intermediate by virtue of the adjacent B atom could result in the chemoselective coupling reaction under ambient conditions.

Entities: Chemical Disease

Year: 2010 PMID： 20698667 DOI： 10.1021/ja105176v

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

25 in total

1. Stereospecific cross-coupling of secondary alkyl β-trifluoroboratoamides.

Authors: Deidre L Sandrock; Ludivine Jean-Gérard; Cheng-yi Chen; Spencer D Dreher; Gary A Molander
Journal: J Am Chem Soc Date: 2010-11-15 Impact factor: 15.419

Review 2. Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Authors: Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal: Chem Rev Date: 2015-08-13 Impact factor: 60.622

Chemoselective and regiospecific Suzuki coupling on a multisubstituted sp(3)-carbon in 1,1-diborylalkanes at room temperature.

1. Stereospecific cross-coupling of secondary alkyl β-trifluoroboratoamides.

Review 2. Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

3. A Boron Alkylidene-Alkene Cycloaddition Reaction: Application to the Synthesis of Aphanamal.

4. Cobalt-Catalyzed 1,1-Diboration of Terminal Alkynes: Scope, Mechanism, and Synthetic Applications.

5. Enantio- and Diastereoselective 1,2-Additions to α-Ketoesters with Diborylmethane and Substituted 1,1-Diborylalkanes.

6. Ketone Synthesis from Benzyldiboronates and Esters: Leveraging α-Boryl Carbanions for Carbon-Carbon Bond Formation.

7. Enantio- and Diastereoselective Synthesis of Hydroxy Bis(boronates) via Cu-Catalyzed Tandem Borylation/1,2-Addition.

8. Enantioselective preparation and chemoselective cross-coupling of 1,1-diboron compounds.

9. Stereoselectivity in Pd-catalysed cross-coupling reactions of enantioenriched nucleophiles.

10. Cobalt-Catalyzed Stereoretentive Hydrogen Isotope Exchange of C(sp³)-H Bonds.