Literature DB >> 27312868

Palladium Catalysis Enables Benzylation of α,α-Difluoroketone Enolates.

Ming-Hsiu Yang1, Jordan R Hunt1, Niusha Sharifi2, Ryan A Altman3.   

Abstract

A palladium-catalyzed decarboxylative benzylation reaction of α,α-difluoroketone enolates is reported, in which the key C(α)-C(sp(3) ) bond is generated by reductive elimination from a palladium intermediate. The transformation provides convergent access to α-benzyl-α,α-difluoroketone-based products, and should be useful for accessing biological probes.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  chemoselectivity; fluorine; palladium; reaction mechanisms; synthetic methods

Mesh：

Substances：

Year:  2016        PMID： 27312868      PMCID： PMC4972046          DOI： 10.1002/anie.201604149

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  9 in total

Review 1.  Transition metal-catalyzed decarboxylative allylation and benzylation reactions.

Authors:  Jimmie D Weaver; Antonio Recio; Alexander J Grenning; Jon A Tunge
Journal:  Chem Rev       Date:  2011-01-14       Impact factor: 60.622

2.  Structure and reactivity of late transition metal η³-benzyl complexes.

Authors:  Barry M Trost; Lara C Czabaniuk
Journal:  Angew Chem Int Ed Engl       Date:  2014-02-19       Impact factor: 15.336

3.  Ligand-controlled regiodivergent palladium-catalyzed decarboxylative allylation reaction to access α,α-difluoroketones.

Authors:  Ming-Hsiu Yang; Douglas L Orsi; Ryan A Altman
Journal:  Angew Chem Int Ed Engl       Date:  2015-01-07       Impact factor: 15.336

4.  Dialkylbiaryl Phosphines in Pd-Catalyzed Amination: A User's Guide.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2011       Impact factor: 9.825

5.  Decarboxylative benzylations of alkynes and ketones.

Authors:  Robert R P Torregrosa; Yamuna Ariyarathna; Kalicharan Chattopadhyay; Jon A Tunge
Journal:  J Am Chem Soc       Date:  2010-07-14       Impact factor: 15.419

6.  Organocatalytic asymmetric synthesis of 3-difluoroalkyl 3-hydroxyoxindoles.

Authors:  Yun-Lin Liu; Jian Zhou
Journal:  Chem Commun (Camb)       Date:  2012-01-09       Impact factor: 6.222

7.  Evaluation of difluoromethyl ketones as agonists of the γ-aminobutyric acid type B (GABAB) receptor.

Authors:  Changho Han; Amy E Salyer; Eun Hoo Kim; Xinyi Jiang; Rachel E Jarrard; Matthew S Powers; Aaron M Kirchhoff; Tolani K Salvador; Julia A Chester; Gregory H Hockerman; David A Colby
Journal:  J Med Chem       Date:  2013-03-06       Impact factor: 7.446

8.  Effect of fluorine on palladium-catalyzed cross-coupling reactions of aryl bromides with trifluoromethyl aryl ketones via difluoroenol silyl or monofluoroenol silyl ethers.

Authors:  Yong Guo; Jean'ne M Shreeve
Journal:  Chem Commun (Camb)       Date:  2007-09-14       Impact factor: 6.222

9.  Pd-catalyzed α-arylation of α,α-difluoroketones with aryl bromides and chlorides. A route to difluoromethylarenes.

Authors:  Shaozhong Ge; Wojciech Chaładaj; John F Hartwig
Journal:  J Am Chem Soc       Date:  2014-03-10       Impact factor: 15.419
  9 in total
  5 in total

1.  Nickel-Catalyzed Decarbonylative Synthesis of Fluoroalkyl Thioethers.

Authors:  Conor E Brigham; Christian A Malapit; Naish Lalloo; Melanie S Sanford
Journal:  ACS Catal       Date:  2020-07-17       Impact factor: 13.084

2.  Decarbonylative Fluoroalkylation at Palladium(II): From Fundamental Organometallic Studies to Catalysis.

Authors:  Naish Lalloo; Christian A Malapit; S Maryamdokht Taimoory; Conor E Brigham; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2021-10-28       Impact factor: 15.419

3.  Synthesis, Biological Evaluation, and Docking Studies of Antagonistic Hydroxylated Arecaidine Esters Targeting mAChRs.

Authors:  Jonas Kilian; Marlon Millard; Marius Ozenil; Dominik Krause; Khadija Ghaderi; Wolfgang Holzer; Ernst Urban; Helmut Spreitzer; Wolfgang Wadsak; Marcus Hacker; Thierry Langer; Verena Pichler
Journal:  Molecules       Date:  2022-05-16       Impact factor: 4.927

4.  Organophotoredox/palladium dual catalytic decarboxylative Csp3-Csp3 coupling of carboxylic acids and π-electrophiles.

Authors:  Kaitie C Cartwright; Jon A Tunge
Journal:  Chem Sci       Date:  2020-07-16       Impact factor: 9.825

5.  Connecting remote C-H bond functionalization and decarboxylative coupling using simple amines.

Authors:  Francisco de Azambuja; Ming-Hsiu Yang; Taisiia Feoktistova; Manikandan Selvaraju; Alexander C Brueckner; Markas A Grove; Suvajit Koley; Paul Ha-Yeon Cheong; Ryan A Altman
Journal:  Nat Chem       Date:  2020-03-09       Impact factor: 24.427
  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.