Online citations, reference lists, and bibliographies.
← Back to Search

Room Temperature Aryl Trifluoromethylation Via Copper-mediated Oxidative Cross-coupling.

Todd D. Senecal, A. T. Parsons, S. L. Buchwald
Published 2011 · Chemistry, Medicine

Cite This
Download PDF
Analyze on Scholarcy
Share
A method for the room temperature copper-mediated trifluoromethylation of aryl and heteroaryl boronic acids has been developed. This protocol is amenable to normal benchtop setup and reactions typically require only 1-4 h. Proceeding under mild conditions, the method tolerates a range of functional groups, allowing access to a variety of trifluoromethylarenes.
This paper references



This paper is referenced by
10.1021/jo202201w
Diverse trifluoromethyl heterocycles from a single precursor.
Mark A. Honey (2012)
10.1039/c3ob41247d
A synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones using CF(3)SiMe(3) as a trifluoromethylating agent.
Chonticha Masusai (2013)
10.1021/jo401423h
Trifluoromethylation of aryl and heteroaryl halides with fluoroform-derived CuCF3: scope, limitations, and mechanistic features.
A. Lishchynskyi (2013)
10.1021/acs.orglett.5b02512
Palladium-Catalyzed Intermolecular Aryldifluoroalkylation of Alkynes.
Y. He (2015)
10.1002/anie.201106742
Palladium-catalyzed 2,2,2-trifluoroethylation of organoboronic acids and esters.
Yanchuan Zhao (2012)
10.1039/c2cc35037h
A Weinreb amide approach to the synthesis of trifluoromethylketones.
D. M. Rudzinski (2012)
10.3762/bjoc.11.286
Carbon–carbon bond cleavage for Cu-mediated aromatic trifluoromethylations and pentafluoroethylations
Tsuyuka Sugiishi (2015)
10.1016/J.JFLUCHEM.2016.07.021
Copper-mediated aerobic iodination and perfluoroalkylation of boronic acids with (CF3)2CFI at room temperature
Xi-Hai Liu (2016)
10.1039/c4cc04930f
Trifluoromethylation of arenediazonium salts with fluoroform-derived CuCF3 in aqueous media.
A. Lishchynskyi (2014)
10.1002/chem.201202853
Copper-catalyzed nucleophilic trifluoromethylation of allylic halides: a simple approach to allylic trifluoromethylation.
Y. Miyake (2012)
10.1021/jo501221h
Copper-free direct C-H trifluoromethylation of acetanilides with sodium trifluoromethanesulfinate.
M. Wu (2014)
10.1002/cctc.201601068
Heterogeneous Chitosan@Copper(II)‐Catalyzed Remote Trifluoromethylation of Aminoquinolines with the Langlois Reagent by Radical Cross‐Coupling
Chao Shen (2016)
10.1002/EJOC.201201244
Highly Efficient Construction of Trifluoromethylated Heterocycles; [3+2] Annulation of N,N′-Cyclic or C,N-Cyclic Azomethine Imines with Trifluoromethyl-Containing Electron-Deficient Olefins
De Wang (2013)
10.1002/EJOC.201301512
A Metal‐Free Route to CF3‐Containing Oxindoles by PhI(OAc)2‐Mediated Trifluoromethylation of N‐Arylacrylamides with TMSCF3
Weijun Fu (2014)
10.1002/anie.201510558
Oxidative Coupling of Aryl Boron Reagents with sp(3)-Carbon Nucleophiles: The Enolate Chan-Evans-Lam Reaction.
Patrick J Moon (2016)
10.1039/C7GC03721J
A solvent-free, base-catalyzed domino reaction towards trifluoromethylated benzenes from bio-based methyl coumalate
Liang Chang (2018)
10.1002/anie.201913878
Fluorous Corannulenes: Ab initio Predictions and the Synthesis of sym-Pentafluorocorannulene.
J. Siegel (2019)
10.1021/ol3022726
Practical method for the Cu-mediated trifluoromethylation of arylboronic acids with CF3 radicals derived from NaSO2CF3 and tert-butyl hydroperoxide (TBHP).
Yingda Ye (2012)
10.1021/ja312711c
Silver-mediated trifluoromethylation-iodination of arynes.
曾裕文 (2013)
10.1002/chem.201303828
Direct synthesis of a trifluoromethyl copper reagent from trifluoromethyl ketones: application to trifluoromethylation.
Hiroki Serizawa (2013)
10.1021/ol501967c
Efficient copper-catalyzed trifluoromethylation of aromatic and heteroaromatic iodides: the beneficial anchoring effect of borates.
Zsombor Gonda (2014)
10.1039/C5QO00044K
Copper-catalyzed stereoselective oxytrifluoromethylation of propargyl amides for the construction of oxazolines
Yanan Wang (2015)
10.1002/0471264180.OR091.01
Nucleophilic Additions of Perfluoroalkyl Groups
P. Beier (2016)
10.1039/C3RA46837B
Copper-mediated trifluoromethylation of aryl-, heteroaryl-, and vinyltrifluoroborates with Langlois' reagent
S. R. Dubbaka (2014)
10.1007/s11244-012-9824-0
Towards a Practical and Efficient Copper-Catalyzed Trifluoromethylation of Aryl Halides
T. Schareina (2012)
10.1021/ja206330m
Copper-catalyzed trifluoromethylation of terminal alkenes through allylic C-H bond activation.
J. Xu (2011)
10.1002/anie.201201613
Fluoroform-derived CuCF3 for low-cost, simple, efficient, and safe trifluoromethylation of aryl boronic acids in air.
P. Novâk (2012)
10.1021/ol302814x
Palladium-catalyzed trifluoromethylation of aromatic C-H bond directed by an acetamino group.
L. Zhang (2013)
10.1021/acs.orglett.6b00142
Silver-Mediated Trifluoromethylthiolation-Iodination of Arynes.
Yuwen Zeng (2016)
10.1002/anie.201302673
Copper-catalyzed trifluoromethylation-initiated radical 1,2-aryl migration in α,α-diaryl allylic alcohols.
Xiaowu Liu (2013)
10.1039/C3SC52548A
Effect of the trifluoromethyl group on torquoselectivity in the 4π ring-opening reaction of oxetenes: stereoselective synthesis of tetrasubstituted olefins
Kohsuke Aikawa (2014)
10.1002/047084289X.RN01755
(1,10‐Phenanthroline)(trifluoromethyl)copper (I)
Feng-Ling Qing (2015)
See more
Semantic Scholar Logo Some data provided by SemanticScholar