Literature DB >> 32099267

Nucleophilic Addition of Benzylboronates to Activated Ketones.

Jacob C Hayes1, Michael R Hollerbach1, Timothy J Barker1.   

Abstract

A method has been developed for the addition of benzylboronic acid pinacol ester to activated ketones including trifluoromethyl ketones in good yields. The use of DABCO as an additive was found to enhance the rate and efficiency of this reaction. In reactions of ketones with a second carbonyl group present such as an ester or amide, good chemoselectivity for the ketone was observed. Competition experiments suggest an electrophile relative reactivity order of CF2H ketone > CF3 ketone > aldehyde under these reaction conditions.

Entities:  

Keywords:  Alkylboronic esters; Boron; Lewis Base; Trifluoromethyl ketone

Year:  2019        PMID： 32099267      PMCID： PMC7041909          DOI： 10.1016/j.tetlet.2019.151505

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  19 in total

1.  Ate complexes of secondary boronic esters as chiral organometallic-type nucleophiles for asymmetric synthesis.

Authors:  Robin Larouche-Gauthier; Tim G Elford; Varinder K Aggarwal
Journal:  J Am Chem Soc       Date:  2011-10-04       Impact factor: 15.419

2.  Trifluoromethyl group as a pharmacophore: effect of replacing a CF3 group on binding and agonist activity of a glucocorticoid receptor ligand.

Authors:  Raj Betageri; Yan Zhang; Renee M Zindell; Daniel Kuzmich; Thomas M Kirrane; Jörg Bentzien; Mario Cardozo; Alison J Capolino; Tazmeen N Fadra; Richard M Nelson; Zofia Paw; Daw-Tsun Shih; Cheng-Kon Shih; Ljiljana Zuvela-Jelaska; Gerald Nabozny; David S Thomson
Journal:  Bioorg Med Chem Lett       Date:  2005-11-01       Impact factor: 2.823

3.  Trifluoromethyl ketones: properties, preparation, and application.

Authors:  Christopher B Kelly; Michael A Mercadante; Nicholas E Leadbeater
Journal:  Chem Commun (Camb)       Date:  2013-10-25       Impact factor: 6.222

4.  Structure and reactivity of boron-ate complexes derived from primary and secondary boronic esters.

Authors:  Kathryn Feeney; Guillaume Berionni; Herbert Mayr; Varinder K Aggarwal
Journal:  Org Lett       Date:  2015-05-14       Impact factor: 6.005

5.  Development of (Trifluoromethyl)zinc Reagent as Trifluoromethyl Anion and Difluorocarbene Sources.

Authors:  Kohsuke Aikawa; Wataru Toya; Yuzo Nakamura; Koichi Mikami
Journal:  Org Lett       Date:  2015-10-02       Impact factor: 6.005

6.  [Study on antiimplantation drugs. II. Synthesis of 1-trifluoromethyl-1,2- diphenylethylenes (author's transl)].

Authors:  Y Q Zhu; S Z Zheng
Journal:  Yao Xue Xue Bao       Date:  1981-04

7.  Chemoselective Benzylation of Aldehydes Using Lewis Base Activated Boronate Nucleophiles.

Authors:  Michael R Hollerbach; Timothy J Barker
Journal:  Organometallics       Date:  2018-04-27       Impact factor: 3.876

8.  Stereospecific functionalizations and transformations of secondary and tertiary boronic esters.

Authors:  Christopher Sandford; Varinder K Aggarwal
Journal:  Chem Commun (Camb)       Date:  2017-05-17       Impact factor: 6.222

9.  Taking the F out of FLP: simple Lewis acid-base pairs for mild reductions with neutral boranes via borenium ion catalysis.

Authors:  Patrick Eisenberger; Adrian M Bailey; Cathleen M Crudden
Journal:  J Am Chem Soc       Date:  2012-10-10       Impact factor: 15.419

Review 10.  Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).

Authors:  Jiang Wang; María Sánchez-Roselló; José Luis Aceña; Carlos del Pozo; Alexander E Sorochinsky; Santos Fustero; Vadim A Soloshonok; Hong Liu
Journal:  Chem Rev       Date:  2013-12-03       Impact factor: 60.622
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  2 in total

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

Authors:  Richard W Russell; Timothy J Barker
Journal:  European J Org Chem       Date:  2021-04-23

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

Authors:  Sophia G Gierszal; Timothy J Barker
Journal:  Tetrahedron Lett       Date:  2021-09-07       Impact factor: 2.032
  2 in total

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