Org Lett. 2010 Oct 1;12(19):4388-91.

Room temperature palladium-catalyzed cross coupling of aryltrimethylammonium triflates with aryl Grignard reagents.

Reeves JT, Fandrick DR, Tan Z, Song JJ, Lee H, Yee NK, Senanayake CH.

Source

Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, USA. jonathan.reeves@boehringer-ingelheim.com

Abstract

Aryltrimethylammonium triflates and tetrafluoroborates were found to be highly reactive electrophiles in the Pd-catalyzed cross coupling with aryl Grignard reagents. The coupling reactions proceed at ambient temperature with a nearly stoichiometric quantity of Grignard reagent, and diverse functionality is tolerated. Competition experiments established the reactivity of PhNMe(3)OTf relative to PhCl, PhBr, PhI, and PhOTf.

PMID:: 20812668; [PubMed - indexed for MEDLINE]

MeSH Terms, Substances

MeSH Terms

Substances

LinkOut - more resources

Full Text Sources

Other Literature Sources

Labome Researcher Resource - ExactAntigen/Labome

Molecular Biology Databases

PALLADIUM - HSDB

Supplemental Content

Related citations

Preparation and palladium-catalyzed cross-coupling of aryl triethylammonium bis(catechol) silicates with aryl triflates. [J Org Chem. 2004]
Preparation and palladium-catalyzed cross-coupling of aryl triethylammonium bis(catechol) silicates with aryl triflates.
Seganish WM, DeShong P. J Org Chem. 2004 Feb 20; 69(4):1137-43.
Palladium-catalyzed cross-coupling reaction of tricyclopropylbismuth with aryl halides and triflates. [J Org Chem. 2008]
Palladium-catalyzed cross-coupling reaction of tricyclopropylbismuth with aryl halides and triflates.
Gagnon A, Duplessis M, Alsabeh P, Barabé F. J Org Chem. 2008 May 2; 73(9):3604-7. Epub 2008 Mar 26.
The development of versatile methods for palladium-catalyzed coupling reactions of aryl electrophiles through the use of P(t-Bu)3 and PCy3 as ligands. [Acc Chem Res. 2008]
The development of versatile methods for palladium-catalyzed coupling reactions of aryl electrophiles through the use of P(t-Bu)3 and PCy3 as ligands.
Fu GC. Acc Chem Res. 2008 Nov 18; 41(11):1555-64.
Review Cross-coupling reactions of organosilicon compounds: new concepts and recent advances. [Chem Pharm Bull (Tokyo). 2002]
Review Cross-coupling reactions of organosilicon compounds: new concepts and recent advances.
Denmark SE, Sweis RF. Chem Pharm Bull (Tokyo). 2002 Dec; 50(12):1531-41.
Review Palladium-catalyzed coupling reactions of aryl chlorides. [Angew Chem Int Ed Engl. 2002]
Review Palladium-catalyzed coupling reactions of aryl chlorides.
Littke AF, Fu GC. Angew Chem Int Ed Engl. 2002 Nov 15; 41(22):4176-211.

See reviews... See all...

Chemical compound information

methyl triflate

MW: 164.10 g/mol

MF: C₂H₃F₃O₃S

See all (3)...

Related information

Related Citations
Calculated set of PubMed citations closely related to the selected article(s) retrieved using a word weight algorithm. Related articles are displayed in ranked order from most to least relevant, with the “linked from” citation displayed first.
Compound (MeSH Keyword)
PubChem chemical compound records that are classified under the same Medical Subject Headings (MeSH) controlled vocabulary as the current articles.
Substance (MeSH Keyword)
PubChem chemical substance (submitted) records that are classified under the same Medical Subject Headings (MeSH) controlled vocabulary as the current articles.

Recent activity

Clear Turn Off Turn On

Room temperature palladium-catalyzed cross coupling of aryltrimethylammonium tri...
Room temperature palladium-catalyzed cross coupling of aryltrimethylammonium triflates with aryl Grignard reagents.
Org Lett. 2010 Oct 1 ;12(19):4388-91.

PubMed
Damned if you do, damned if you don't: potassium binding resins in hyperkalemia.
Damned if you do, damned if you don't: potassium binding resins in hyperkalemia.
Clin J Am Soc Nephrol. 2010 Oct ;5(10):1723-6. Epub 2010 Aug 26 .

PubMed
Levonorgestrel-releasing intrauterine system or medroxyprogesterone for heavy me...
Levonorgestrel-releasing intrauterine system or medroxyprogesterone for heavy menstrual bleeding: a randomized controlled trial.
Obstet Gynecol. 2010 Sep ;116(3):625-32.

PubMed
Ezetimibe reduces enlarged prostate in an animal model of benign prostatic hyper...
Ezetimibe reduces enlarged prostate in an animal model of benign prostatic hyperplasia.
J Urol. 2010 Oct ;184(4):1555-9. Epub 2010 Aug 21 .

PubMed
A Method to Detect Differential Gene expression in Cross-Species Hybridization E...
A Method to Detect Differential Gene expression in Cross-Species Hybridization Experiments at Gene and Probe Level.
Biomed Inform Insights. 2010 Mar 5;2010(3):1-10.

PubMed

Your browsing activity is empty.

Activity recording is turned off.

Turn recording back on

PubMed

Display Settings:

Send to: