+ Site Statistics
+ Search Articles
+ Subscribe to Site Feeds
EurekaMag Most Shared ContentMost Shared
EurekaMag PDF Full Text ContentPDF Full Text
+ PDF Full Text
Request PDF Full TextRequest PDF Full Text
+ Follow Us
Follow on FacebookFollow on Facebook
Follow on TwitterFollow on Twitter
Follow on Google+Follow on Google+
Follow on LinkedInFollow on LinkedIn

+ Translate

Regioselective alkynylation followed by Suzuki coupling of 2,4-dichloroquinoline: synthesis of 2-alkynyl-4-arylquinolines

Beilstein Journal of Organic Chemistry 5: 32-32

Regioselective alkynylation followed by Suzuki coupling of 2,4-dichloroquinoline: synthesis of 2-alkynyl-4-arylquinolines

A two step synthesis of 2-alkynyl-4-arylquinolines has been accomplished via Pd/C-mediated regioselective C-2 alkynylation of 2,4-dichloroquinoline in water followed by Suzuki coupling at C-4 of the resulting 4-chloro derivative.

Accession: 055445533

PMID: 19777134

DOI: 10.3762/bjoc.5.32

Related references

Zhang, Y.; Gao, J.; Li, W.; Lee, H.; Lu, B.Z.; Senanayake, C.H., 2012: Synthesis of 8-arylquinolines via one-pot Pd-catalyzed borylation of quinoline-8-yl halides and subsequent Suzuki-Miyaura coupling. A one-pot process has been developed for the synthesis of 8-arylquinolines via Pd-catalyzed borylation of quinoline-8-yl halides and subsequent Suzuki-Miyaura coupling with aryl halides using n-BuPAd(2) as ligand. Yields of up to 98% were obtained...

Ma, Y.; Zhang, S.; Yang, S.; Song, F.; You, J., 2014: Gold-catalyzed C(sp3)-H/C(sp)H coupling/cyclization/oxidative alkynylation sequence: a powerful strategy for the synthesis of 3-alkynyl polysubstituted furans. In sharp contrast to the gold-catalyzed reactions of alkynes/allenes with nucleophiles, gold-catalyzed oxidative cross-couplings and especially C-H/C-H cross-coupling have been under represented. By taking advantage of the unique redox property an...

Tagata, T.; Nishida, M., 2003: Palladium charcoal-catalyzed Suzuki-Miyaura coupling to obtain arylpyridines and arylquinolines. A phosphine ligand, such as PPh3 or 2-(dicyclohexylphosphino)biphenyl, is essential for the Pd/C-catalyzed Suzuki-Miyaura coupling of halopyridines and haloquinolines, although it has been reported that the reaction of phenyl chlorides can be cata...

Sun, F.; Gu, Z., 2015: Decarboxylative Alkynyl Termination of Palladium-Catalyzed Catellani Reaction: A Facile Synthesis of α-Alkynyl Anilines via Ortho C-H Amination and Alkynylation. A palladium-catalyzed synthesis of α-alkynyl anilines is reported. The reaction proceeds via Catellani ortho C-H amination followed by decarboxylative alkynylative amination. Different terminal alkyne precursors were screened, and it was found th...

Grégory Burzicki; Anne Sophie Voisin-Chiret; Jana Sopkovà-de Oliveira Santos; Sylvain Rault, 2009: Synthesis of Dihalo Bi- and Terpyridines by Regioselective Suzuki-Miyaura Cross-Coupling Reactions. This paper describes an efficient and regioselective synthetic route leading to new dihalobi- and terpyridines. We developed a strategy based on regioselective sequence of Suzuki–Miyaura cross-coupling reactions between bromopyridyl boronic...

Yang, W.; Wang, Y.; Corte, J.R., 2003: Efficient synthesis of 2-aryl-6-chloronicotinamides via PXPd2-catalyzed regioselective Suzuki coupling. [reaction: see text] A short and convergent synthesis of 2-aryl-6-chloronicotinamides via regioselective Suzuki coupling of 2,6-dichloronicotinamide with aryl boronic acids is described. Regioselectivity was achieved by chelation of the palladium(...

Jørgensen, Kåre.B.; Rantanen, T.; Dörfler, T.; Snieckus, V., 2015: Directed Metalation-Suzuki-Miyaura Cross-Coupling Strategies: Regioselective Synthesis of Hydroxylated 1-Methyl-phenanthrenes. A general, efficient, and regioselective synthesis of a series of hydroxylated 1-methylphenanthrenes 9 by a combined directed ortho metalation (DoM)-Suzuki-Miyaura cross-coupling-directed remote metalation (DreM) sequence is reported. Diversity to...

Grob, J.E.; Nunez, J.; Dechantsreiter, M.A.; Hamann, L.G., 2012: Regioselective synthesis and slow-release Suzuki-Miyaura cross-coupling of MIDA boronate-functionalized isoxazoles and triazoles. The efficient preparation of heterocycles with a range of substitutions ortho to heteroatoms remains as a challenge in organic synthesis, particularly relevant to the construction of druglike molecules due to the ubiquitous presence of such moieti...

Rizwan, K.; Zubair, M.; Rasool, N.; Ali, S.; Zahoor, A.Fawad.; Rana, U.Ali.; Khan, S.Ud-Din.; Shahid, M.; Zia-Ul-Haq, M.; Jaafar, H.Ze., 2015: Regioselective synthesis of 2-(bromomethyl)-5-aryl-thiophene derivatives via palladium (0) catalyzed suzuki cross-coupling reactions: as antithrombotic and haemolytically active molecules. It is seen that the regioselective functionalizations of halogenated heterocycles play an important role in the synthesis of several types of organic compounds. In this domain, the Suzuki-Miyaura reaction has emerged as a convenient way to build c...

Tiwari, V.Kumar.; Pawar, G.Goroba.; Das, R.; Adhikary, A.; Kapur, M., 2013: Heteroatom-guided, palladium-catalyzed regioselective C-H functionalization in the synthesis of 3-arylquinolines. A new approach for the regioselective functionalization of the C-3-position of quinolines is described. The method utilizes heteroatom guided regioselective C-3 palladation followed by arylation via transmetalation with aryl boronic acids to yield...