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Literature DB >> 34404720

Electrochemical borylation of carboxylic acids.

Lisa M Barton¹, Longrui Chen¹, Donna G Blackmond², Phil S Baran².

Abstract

A simple electrochemically mediated method for the conversion of alkyl carboxylic acids to their borylated congeners is presented. This protocol features an undivided cell setup with inexpensive carbon-based electrodes and exhibits a broad substrate scope and scalability in both flow and batch reactors. The use of this method in challenging contexts is exemplified with a modular formal synthesis of jawsamycin, a natural product harboring five cyclopropane rings.

Entities: Chemical

Keywords: electrochemistry; organic synthesis; total synthesis

Mesh：

Substances：

Year: 2021 PMID： 34404720 PMCID： PMC8403965 DOI： 10.1073/pnas.2109408118

Source DB: PubMed Journal: Proc Natl Acad Sci U S A ISSN： 0027-8424 Impact factor: 11.205

49 in total

Review 1. Synthesis and properties of oligocyclopropyl-containing natural products and model compounds.

Authors: Jörg Pietruszka
Journal: Chem Rev Date: 2003-04 Impact factor: 60.622

Review 2. Reaction progress kinetic analysis: a powerful methodology for mechanistic studies of complex catalytic reactions.

Authors: Donna G Blackmond
Journal: Angew Chem Int Ed Engl Date: 2005-07-11 Impact factor: 15.336

3. Decarboxylative borylation.

Authors: Chao Li; Jie Wang; Lisa M Barton; Shan Yu; Maoqun Tian; David S Peters; Manoj Kumar; Antony W Yu; Kristen A Johnson; Arnab K Chatterjee; Ming Yan; Phil S Baran
Journal: Science Date: 2017-04-13 Impact factor: 47.728

Review 4. Saturated bioisosteres of benzene: where to go next?

Authors: Pavel K Mykhailiuk
Journal: Org Biomol Chem Date: 2019-03-13 Impact factor: 3.876

5. Manganese-Catalyzed Borylation of Unactivated Alkyl Chlorides.

Authors: Thomas C Atack; Silas P Cook
Journal: J Am Chem Soc Date: 2016-05-09 Impact factor: 15.419

6. Photoinduced Radical Borylation of Alkyl Bromides Catalyzed by 4-Phenylpyridine.

Authors: Li Zhang; Zhong-Qian Wu; Lei Jiao
Journal: Angew Chem Int Ed Engl Date: 2019-12-12 Impact factor: 15.336

7. Nickel-Catalyzed Enantioconvergent Borylation of Racemic Secondary Benzylic Electrophiles.

Authors: Zhaobin Wang; Shoshana Bachman; Alexander S Dudnik; Gregory C Fu
Journal: Angew Chem Int Ed Engl Date: 2018-08-19 Impact factor: 15.336

8. Zinc-catalyzed borylation of primary, secondary and tertiary alkyl halides with alkoxy diboron reagents at room temperature.

Authors: Shubhankar Kumar Bose; Katharina Fucke; Lei Liu; Patrick G Steel; Todd B Marder
Journal: Angew Chem Int Ed Engl Date: 2014-01-13 Impact factor: 15.336

Electrochemical borylation of carboxylic acids.

Review 1. Synthesis and properties of oligocyclopropyl-containing natural products and model compounds.

Review 2. Reaction progress kinetic analysis: a powerful methodology for mechanistic studies of complex catalytic reactions.

3. Decarboxylative borylation.

Review 4. Saturated bioisosteres of benzene: where to go next?

5. Manganese-Catalyzed Borylation of Unactivated Alkyl Chlorides.

6. Photoinduced Radical Borylation of Alkyl Bromides Catalyzed by 4-Phenylpyridine.

7. Nickel-Catalyzed Enantioconvergent Borylation of Racemic Secondary Benzylic Electrophiles.

8. Zinc-catalyzed borylation of primary, secondary and tertiary alkyl halides with alkoxy diboron reagents at room temperature.

9. A Simple Graphical Method to Determine the Order in Catalyst.

10. Cu-Catalyzed Decarboxylative Borylation.

1. Regio- and Stereoselective Electrochemical Alkylation of Morita-Baylis-Hillman Adducts.

2. Electrochemically Mediated Oxidation of Sensitive Propargylic Benzylic Alcohols.