Science 2010-06-25

The palladium-catalyzed trifluoromethylation of aryl chlorides.

Eun Jin Cho, Todd D Senecal, Tom Kinzel, Yong Zhang, Donald A Watson, Stephen L Buchwald

Index: Science 328 , 1679-1681, (2010)

Full Text: HTML

Abstract

The trifluoromethyl group can dramatically influence the properties of organic molecules, thereby increasing their applicability as pharmaceuticals, agrochemicals, or building blocks for organic materials. Despite the importance of this substituent, no general method exists for its installment onto functionalized aromatic substrates. Current methods either require the use of harsh reaction conditions or suffer from a limited substrate scope. Here we report the palladium-catalyzed trifluoromethylation of aryl chlorides under mild conditions, allowing the transformation of a wide range of substrates, including heterocycles, in excellent yields. The process tolerates functional groups such as esters, amides, ethers, acetals, nitriles, and tertiary amines and, therefore, should be applicable to late-stage modifications of advanced intermediates. We have also prepared all the putative intermediates in the catalytic cycle and demonstrated their viability in the process.


Related Compounds

Related Articles:

Utilizing capillary gas chromatography mass spectrometry to determine 4-benzotrifluoride t-butyl ether as a reaction by-product in fluoxetine synthesized using potassium t-butoxide as base.

2003-02-05

[J. Pharm. Biomed. Anal. 31(1) , 63-74, (2003)]

Study of the voltammetric behaviour of the ethalfluralin and methalpropalin and its determination in environmental matrices at hanging mercury drop electrode.

2004-01-01

[Environ. Monit. Assess. 151(1-4) , 9-18, (2009)]

Precursor chemistry matters in boosting photoredox activity of graphene/semiconductor composites.

2015-11-21

[Nanoscale 7 , 18062-70, (2015)]

Accelerated separation of GC-amenable lipid classes in plant oils by countercurrent chromatography in the co-current mode.

2015-12-01

[Anal. Bioanal. Chem 407 , 9019-28, (2015)]

An integrated microreactor system for self-optimization of a Heck reaction: from micro- to mesoscale flow systems.

2010-09-17

[Angew. Chem. Int. Ed. Engl. 49(39) , 7076-80, (2010)]

More Articles...