Letter
Palladium-Catalyzed Cross-Coupling of Aryl Electrophiles with Dimethylalkynylaluminum Reagents
Purchase the full-text
- PDF/HTML,
figures/images,
references and tables,
(where available)
Abstract

Alkynyldimethylaluminum reagents are easily available from terminal akynes and trimethylaluminum via a triethylamine-catalyzed metalation. These compounds can react with various aromatic and heterocyclic halides in the presence of palladium in a fast and efficient way. This catalyzed cross-coupling reaction provides a simple entry to numerous internal alkynes, using a readily available, inexpensive, and nontoxic metalating agent.
Citing Articles
Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.
This article has been cited by 8 ACS Journal articles (5 most recent appear below).

Direct Synthesis of Polysubstituted Aluminoisoxazoles and Pyrazoles by a Metalative Cyclization
Olivier Jackowski, Thomas Lecourt, and Laurent MicouinOrganic Letters2011 13 (20), 5664-5667Direct Synthesis of Polysubstituted Aluminoisoxazoles and Pyrazoles by a Metalative Cyclization
Olivier Jackowski, Thomas Lecourt, and Laurent MicouinOrganic Letters2011 13 (20), 5664-5667Alumino-heteroles are obtained from simple precursors in a fully chemo- and regioselective manner by a metalative cyclization. The carbon–aluminum bond is still able to react further with several electrophiles, without the need of transmetalation. This ...

Highly Enantioselective Vinyl Additions of Vinylaluminum to Ketones Catalyzed by a Titanium(IV) Catalyst of (S)-BINOL
Deepak Baburao Biradar and Han-Mou GauOrganic Letters2009 11 (3), 499-502Highly Enantioselective Vinyl Additions of Vinylaluminum to Ketones Catalyzed by a Titanium(IV) Catalyst of (S)-BINOL
Deepak Baburao Biradar and Han-Mou GauOrganic Letters2009 11 (3), 499-502We report a novel asymmetric addition of vinyl group to ketones using vinylaluminum reagents catalyzed by in situ prepared Ti(OiPr)4 complexes of (S)-BINOL to afford diversified tertiary allylic alochols. Varieties of aromatic ketones bearing either an ...

Diastereoselective Alkynylation of N-p-Tolylsulfinylimines with Aluminum Acetylides
Serge Turcaud, Farouk Berhal, and Jacques RoyerThe Journal of Organic Chemistry2007 72 (21), 7893-7897Diastereoselective Alkynylation of N-p-Tolylsulfinylimines with Aluminum Acetylides
Serge Turcaud, Farouk Berhal, and Jacques RoyerThe Journal of Organic Chemistry2007 72 (21), 7893-7897The addition of alkynyl dimethyl aluminum compounds onto N-p-tolylsulfinylimines was investigated. The reaction was proved to be totally regioselective, leading to propargylamines with high diastereoselectivity (up to 99% de). Addition of aluminum ...

Asymmetric α-Alkynylation of Piperidine via N-Sulfinyliminium Salts
Serge Turcaud, Emma Sierecki, Thierry Martens, and Jacques RoyerThe Journal of Organic Chemistry2007 72 (13), 4882-4885Asymmetric α-Alkynylation of Piperidine via N-Sulfinyliminium Salts
Serge Turcaud, Emma Sierecki, Thierry Martens, and Jacques RoyerThe Journal of Organic Chemistry2007 72 (13), 4882-4885Piperidine was stereoselectively α-alkynylated in a four-step sequence made up of transformation to a chiral nonracemic N-sulfinylpiperidine, anodic oxidation to N-sulfinyliminium ion equivalent, alkynylation through addition of a mixed organoaluminum ...

Reductive Carbonylation − an Efficient and Practical Catalytic Route for the Conversion of Aryl Halides to Aldehydes
Laura Ashfield and Christopher F. J. BarnardOrganic Process Research & Development2007 11 (1), 39-43Reductive Carbonylation − an Efficient and Practical Catalytic Route for the Conversion of Aryl Halides to Aldehydes
Laura Ashfield and Christopher F. J. BarnardOrganic Process Research & Development2007 11 (1), 39-43Alternative routes for the introduction of aldehyde functionality are particularly desirable for fine chemical and pharmaceutical intermediates because of the wide range of further transformations that are possible. Catalytic processes are of particular ...
Tools
-
Add to Favorites
-
Download Citation
-
Email a Colleague -
Permalink
Order Reprints
Rights & Permissions
Citation Alerts
History
- Published In Issue September 30, 2004
- Received July 2, 2004
Cart

ACS
Network






