Literature DB >> 22111687

The palladium-catalyzed trifluoromethylation of vinyl sulfonates.

Eun Jin Cho1, Stephen L Buchwald.   

Abstract

A method for the palladium-catalyzed trifluoromethylation of cyclohexenyl sulfonates has been developed. Various cyclohexenyl triflates and nonaflates underwent trifluoromethylation under mild reaction conditions using a catalyst system composed of Pd(dba)(2) or [(allyl)PdCl](2) and the monodentate biaryl phosphine ligand (t)BuXPhos. The trifluoromethyl anion (CF(3)(-)) or its equivalent for the process was generated in situ from TMSCF(3) in combination with KF or TESCF(3) in combination with RbF.

Entities:  

Mesh：

Substances：

Year:  2011        PMID： 22111687      PMCID： PMC3242697          DOI： 10.1021/ol202885w

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  27 in total

1.  Perfluoroalkylation with Organosilicon Reagents.

Authors:  G. K. Surya Prakash; Andrei K. Yudin
Journal:  Chem Rev       Date:  1997-05-08       Impact factor: 60.622

2.  Copper-mediated oxidative trifluoromethylation of boronic acids.

Authors:  Lingling Chu; Feng-Ling Qing
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

3.  Antiestrogens, antiandrogens.

Authors:  J Borvendég; I Hermann; O Csuka
Journal:  Acta Physiol Hung       Date:  1996

Review 4.  Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions.

Authors:  Jun-An Ma; Dominique Cahard
Journal:  Chem Rev       Date:  2004-12       Impact factor: 60.622

5.  Facile Ar-CF3 bond formation at Pd. Strikingly different outcomes of reductive elimination from [(Ph3P)2Pd(CF3)Ph] and [(Xantphos)Pd(CF3)Ph].

Authors:  Vladimir V Grushin; William J Marshall
Journal:  J Am Chem Soc       Date:  2006-10-04       Impact factor: 15.419

6.  Copper-catalyzed trifluoromethylation of unactivated olefins.

Authors:  Andrew T Parsons; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2011-08-25       Impact factor: 15.336

7.  Pd(II)-catalyzed ortho-trifluoromethylation of arenes using TFA as a promoter.

Authors:  Xisheng Wang; Larry Truesdale; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2010-03-24       Impact factor: 15.419

8.  Aryl-CF(3) bond-forming reductive elimination from palladium(IV).

Authors:  Nicholas D Ball; Jeff W Kampf; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2010-03-10       Impact factor: 15.419

9.  Copper-catalyzed trifluoromethylation of aryl and vinyl boronic acids with an electrophilic trifluoromethylating reagent.

Authors:  Tianfei Liu; Qilong Shen
Journal:  Org Lett       Date:  2011-04-07       Impact factor: 6.005

10.  Active trifluoromethylating agents from well-defined Copper(I)-CF3 complexes.

Authors:  Galyna G Dubinina; Hideki Furutachi; David A Vicic
Journal:  J Am Chem Soc       Date:  2008-06-11       Impact factor: 15.419
View more
  12 in total

1.  Julia-Kocienski Approach to Trifluoromethyl-Substituted Alkenes1.

Authors:  Deborah O Ayeni; Samir K Mandal; Barbara Zajc
Journal:  Tetrahedron Lett       Date:  2013-11-06       Impact factor: 2.415

2.  Copper-catalyzed oxytrifluoromethylation of unactivated alkenes.

Authors:  Rong Zhu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2012-07-23       Impact factor: 15.419

3.  Monophosphine Ligands Promote Pd-Catalyzed C-S Cross-Coupling Reactions at Room Temperature with Soluble Bases.

Authors:  Jessica Xu; Richard Y Liu; Charles S Yeung; Stephen L Buchwald
Journal:  ACS Catal       Date:  2019-06-21       Impact factor: 13.084

4.  Palladium-Catalyzed Fluorination of Cyclic Vinyl Triflates: Effect of TESCF3 as an Additive.

Authors:  Yuxuan Ye; Takashi Takada; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2016-11-15       Impact factor: 15.336

5.  Palladium-catalyzed intramolecular C-H difluoroalkylation: synthesis of substituted 3,3-difluoro-2-oxindoles.

Authors:  Shi-Liang Shi; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2014-12-04       Impact factor: 15.336

6.  Iron(II)-catalyzed trifluoromethylation of potassium vinyltrifluoroborates.

Authors:  Andrew T Parsons; Todd D Senecal; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2012-02-10       Impact factor: 15.336

7.  Investigating the dearomative rearrangement of biaryl phosphine-ligated Pd(II) complexes.

Authors:  Phillip J Milner; Thomas J Maimone; Mingjuan Su; Jiahao Chen; Peter Müller; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2012-11-27       Impact factor: 15.419

8.  Design and Preparation of New Palladium Precatalysts for C-C and C-N Cross-Coupling Reactions.

Authors:  Nicholas C Bruno; Matthew T Tudge; Stephen L Buchwald
Journal:  Chem Sci       Date:  2013       Impact factor: 9.825

Review 9.  Recent advances in transition metal-catalyzed Csp(2)-monofluoro-, difluoro-, perfluoromethylation and trifluoromethylthiolation.

Authors:  Grégory Landelle; Armen Panossian; Sergiy Pazenok; Jean-Pierre Vors; Frédéric R Leroux
Journal:  Beilstein J Org Chem       Date:  2013-11-15       Impact factor: 2.883

10.  Copper-catalyzed trifluoromethylation of alkenes with an electrophilic trifluoromethylating reagent.

Authors:  Xiao-Ping Wang; Jin-Hong Lin; Cheng-Pan Zhang; Ji-Chang Xiao; Xing Zheng
Journal:  Beilstein J Org Chem       Date:  2013-11-25       Impact factor: 2.883
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.