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Literature DB >> 31680714

Chemoselective Benzylation of Aldehydes Using Lewis Base Activated Boronate Nucleophiles.

Michael R Hollerbach¹, Timothy J Barker¹.

Abstract

A benzylation of aldehydes using primary and secondary benzylboronic acid pinacol esters is reported. Activation of the boronic ester with s-butyllithium rendered it nucleophilic toward aldehydes. The activated nucleophile chemoselectively transfers the benzyl group over the s-butyl group, providing excellent yields of the benzylated products. 11B NMR experiments were performed to study the mechnism of this transformation.

Entities: Chemical Disease Species

Year: 2018 PMID： 31680714 PMCID： PMC6824429 DOI： 10.1021/acs.organomet.8b00085

Source DB: PubMed Journal: Organometallics ISSN： 0276-7333 Impact factor: 3.876

37 in total

1. Iron-catalyzed borylation of alkyl electrophiles.

Authors: Thomas C Atack; Rachel M Lecker; Silas P Cook
Journal: J Am Chem Soc Date: 2014-06-23 Impact factor: 15.419

2. Transmetalation of unsaturated carbon nucleophiles from boron-containing species to the mid to late d-block metals of relevance to catalytic C-X coupling reactions (X = C, F, N, O, Pb, S, Se, Te).

Authors: David V Partyka
Journal: Chem Rev Date: 2011-03-09 Impact factor: 60.622

3. Cross-coupling reactions of organoboranes: an easy way to construct C-C bonds (Nobel Lecture).

Authors: Akira Suzuki
Journal: Angew Chem Int Ed Engl Date: 2011-05-25 Impact factor: 15.336

4. Stereospecific Coupling of Boronic Esters with N-Heteroaromatic Compounds.

Authors: Josep Llaveria; Daniele Leonori; Varinder K Aggarwal
Journal: J Am Chem Soc Date: 2015-08-21 Impact factor: 15.419

5. Highly enantioselective synthesis of tertiary boronic esters and their stereospecific conversion to other functional groups and quaternary stereocentres.

Authors: Helen K Scott; Varinder K Aggarwal
Journal: Chemistry Date: 2011-11-03 Impact factor: 5.236

Review 6. Boron-selective reactions as powerful tools for modular synthesis of diverse complex molecules.

Authors: Liang Xu; Shuai Zhang; Pengfei Li
Journal: Chem Soc Rev Date: 2015-09-22 Impact factor: 54.564

7. Making Dimethylamino a Transformable Directing Group by Nickel-Catalyzed C-N Borylation.

Authors: Hua Zhang; Shinya Hagihara; Kenichiro Itami
Journal: Chemistry Date: 2015-10-05 Impact factor: 5.236

8. Nickel-Catalyzed Borylation of Aryl- and Benzyltrimethylammonium Salts via C-N Bond Cleavage.

Authors: Jiefeng Hu; Heqing Sun; Wangshui Cai; Xinghui Pu; Yemin Zhang; Zhuangzhi Shi
Journal: J Org Chem Date: 2015-12-15 Impact factor: 4.354

9. Iridium-Catalyzed Borylation of Primary Benzylic C-H Bonds without a Directing Group: Scope, Mechanism, and Origins of Selectivity.

Authors: Matthew A Larsen; Conner V Wilson; John F Hartwig
Journal: J Am Chem Soc Date: 2015-06-25 Impact factor: 15.419

Chemoselective Benzylation of Aldehydes Using Lewis Base Activated Boronate Nucleophiles.

1. Iron-catalyzed borylation of alkyl electrophiles.

2. Transmetalation of unsaturated carbon nucleophiles from boron-containing species to the mid to late d-block metals of relevance to catalytic C-X coupling reactions (X = C, F, N, O, Pb, S, Se, Te).

3. Cross-coupling reactions of organoboranes: an easy way to construct C-C bonds (Nobel Lecture).

4. Stereospecific Coupling of Boronic Esters with N-Heteroaromatic Compounds.

5. Highly enantioselective synthesis of tertiary boronic esters and their stereospecific conversion to other functional groups and quaternary stereocentres.

Review 6. Boron-selective reactions as powerful tools for modular synthesis of diverse complex molecules.

7. Making Dimethylamino a Transformable Directing Group by Nickel-Catalyzed C-N Borylation.

8. Nickel-Catalyzed Borylation of Aryl- and Benzyltrimethylammonium Salts via C-N Bond Cleavage.

9. Iridium-Catalyzed Borylation of Primary Benzylic C-H Bonds without a Directing Group: Scope, Mechanism, and Origins of Selectivity.

10. Protodeboronation of tertiary boronic esters: asymmetric synthesis of tertiary alkyl stereogenic centers.

1. Transition Metal Free sp³-sp³ carbon-carbon coupling between Benzylboronic Esters and Alkyl Bromides.

2. Cu-Catalyzed Cross-Coupling of Benzylboronic Esters and Epoxides.

3. Benzylation of Imines with Activated Boronate Nucleophiles.

4. Nucleophilic Addition of Benzylboronates to Activated Ketones.