Convenient methods for preparing pi-conjugated linkers as building blocks for modular chemistry

. 2009 Apr 14 ; 5 () : 11. [epub] 20090414

Status PubMed-not-MEDLINE Jazyk angličtina Země Německo Médium electronic

Typ dokumentu časopisecké články

Perzistentní odkaz   https://www.medvik.cz/link/pmid19478966

Simple, straightforward and optimized procedures for preparing extended pi-conjugated linkers are described. Either unsubstituted or 4-donor substituted pi-linkers bearing a styryl, biphenyl, phenylethenylphenyl, and phenylethynylphenyl pi-conjugated backbone are functionalized with boronic pinacol esters as well as with terminal acetylene moieties allowing their further use as building blocks in Suzuki-Miyaura or Sonogashira coupling reactions.

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Albota M, Beljonne D, Brédas J-L, Ehrlich J E, Fu J-Y, Heikal A A, Hess S E, Kogej T, Levin M D, Marder S R, et al. Science. 1998;281:1653–1656. doi: 10.1126/science.281.5383.1653. PubMed DOI

Marder S R. Chem Commun. 2006:131–134. doi: 10.1039/b512646k. PubMed DOI

Kivala M, Boudon C, Gisselbrecht J-P, Seiler P, Gross M, Diederich F. Angew Chem, Int Ed. 2007;46:6357–6360. doi: 10.1002/anie.200701733. PubMed DOI

Bureš F, Schweizer W B, Boudon C, Gisselbrecht J-P, Gross M, Diederich F. Eur J Org Chem. 2008:994–1004. doi: 10.1002/ejoc.200700970. DOI

Juríček M, Kasák P, Stach M, Putala M. Tetrahedron Lett. 2007;48:8869–8873. doi: 10.1016/j.tetlet.2007.10.044. DOI

Li Z, Qin A, Lam J W Y, Dong Y, Dong Y, Ye C, Williams I D, Tang B Z. Macromolecules. 2006;39:1436–1442. doi: 10.1021/ma051924f. DOI

Cumpston B H, Ananthavel S P, Barlow S, Dyer D L, Ehrlich J E, Erskine L L, Heikal A A, Kuebler S M, Lee I-Y S, McCord-Maughon D, et al. Nature. 1999;398:51–54. doi: 10.1038/17989. DOI

Moonen N N P, Gist R, Boudon C, Gisselbrecht J-P, Seiler P, Kawai T, Kishioka A, Gross M, Irie M, Diederich F. Org Biomol Chem. 2003;1:2032–2034. doi: 10.1039/b303879c. PubMed DOI

Haldi A, Kimyonok A, Domercq B, Hayden L E, Jones S C, Marder S R, Weck M, Kippelen B. Adv Funct Mater. 2008;18:3056–3062. doi: 10.1002/adfm.200800446. DOI

Kraft A, Grimsdale A C, Holmes A B. Angew Chem, Int Ed. 1998;37:402–428. doi: 10.1002/(SICI)1521-3773(19980302)37:4<402::AID-ANIE402>3.0.CO;2-9. PubMed DOI

Ma H, Liu S, Luo J, Suresh S, Liu L, Kang S H, Haller M, Sassa T, Dalton L R, Jen A K-Y. Adv Funct Mater. 2002;12:565–574. doi: 10.1002/1616-3028(20020916)12:9<565::AID-ADFM565>3.0.CO;2-8. DOI

Kivala M, Diederich F. Acc Chem Res. 2009;42:235–248. doi: 10.1021/ar8001238. PubMed DOI

Do J Y, Ju J J. Macromol Chem Phys. 2005;206:1326–1331. doi: 10.1002/macp.200400547. DOI

Pahadi N K, Camacho D H, Nakamura I, Yamamoto Y. J Org Chem. 2006;71:1152–1155. doi: 10.1021/jo052262v. PubMed DOI

Hennrich G, Asselberghs I, Clays K, Persoons A. J Org Chem. 2004;69:5077–5081. doi: 10.1021/jo049279i. PubMed DOI

Wang J, Lu M, Pan Y, Peng Z. J Org Chem. 2002;67:7781–7786. doi: 10.1021/jo026186x. PubMed DOI

Kivala M, Stanoeva T, Michinobu T, Frank B, Gescheidt G, Diederich F. Chem–Eur J. 2008;14:7638–7647. doi: 10.1002/chem.200800716. PubMed DOI

Spitler E L, Shirtcliff L D, Haley M H. J Org Chem. 2007;72:86–96. doi: 10.1021/jo061712w. PubMed DOI

Patel A, Bureš F, Ludwig M, Kulhánek J, Pytela O, Růžička A. Heterocycles. 2009;78:999–1013. doi: 10.3987/COM-08-11609. DOI

Batista R M F, Costa S P G, Belsley M, Lodeiro C, Raposo M M M. Tetrahedron. 2008;64:9230–9238. doi: 10.1016/j.tet.2008.07.043. DOI

Bureš F, Schweizer W B, May J C, Boudon C, Gisselbrecht J-P, Gross M, Biaggio I, Diederich F. Chem–Eur J. 2007;13:5378–5387. doi: 10.1002/chem.200601735. PubMed DOI

Andersson A S, Kerndrup L, Madsen A Ø, Kilså K, Nielsen M B, La Porta P R, Biaggio I. J Org Chem. 2009;74:375–382. doi: 10.1021/jo802190q. PubMed DOI

May J C, Biaggio I, Bureš F, Diederich F. Appl Phys Lett. 2007;90:No. 251106. doi: 10.1063/1.2750396. DOI

Wan J-H, Feng J-C, Wen G-A, Wei W, Fan Q-L, Wang C-M, Wang H-Y, Zhu R, Yuan X-D, Huang C-H, et al. J Org Chem. 2006;71:2565–2571. doi: 10.1021/jo0521596. PubMed DOI

Bureš F, Pytela O, Diederich F. J Phys Org Chem. 2009;22:155–162. doi: 10.1002/poc.1443. DOI

Miyaura N, Suzuki A. Chem Rev. 1995;95:2457–2483. doi: 10.1021/cr00039a007. DOI

Kotha S, Lahiri K, Kashinath D. Tetrahedron. 2002;58:9633–9695. doi: 10.1016/S0040-4020(02)01188-2. DOI

Chinchilla R, Nájera C. Chem Rev. 2007;107:874–922. doi: 10.1021/cr050992x. PubMed DOI

Murata M, Watanabe S, Masuda Y. J Org Chem. 1997;62:6458–6459. doi: 10.1021/jo970963p. PubMed DOI

Elangovan A, Wang Y-H, Ho T-I. Org Lett. 2003;5:1841–1844. doi: 10.1021/ol034320+. PubMed DOI

Mkhalid I A I, Coapes R B, Edes S N, Coventry D N, Souza F E S, Thomas R L, Hall J J, Bi S-W, Lin Z, Marder T B. Dalton Trans. 2008:1055–1064. doi: 10.1039/b715584k. PubMed DOI

Murata M, Kawakita K, Asana T, Watanabe S, Masuda Y. Bull Chem Soc Jpn. 2002;75:825–829. doi: 10.1246/bcsj.75.825. DOI

Perner R J, Lee C-H, Jiang M, Gu Y-G, DiDomenico S, Bayburt E K, Alexander K M, Kohlhaas K L, Jarvis M F, Kowaluk E L, et al. Bioorg Med Chem Lett. 2005;15:2803–2807. doi: 10.1016/j.bmcl.2005.03.098. PubMed DOI

Itami K, Tonogaki K, Ohashi Y, Yoshida J-i. Org Lett. 2004;6:4093–4096. doi: 10.1021/ol048217b. PubMed DOI

Chaumeil H, Le Drian C, Defoin A. Synthesis. 2002:757–760. doi: 10.1055/s-2002-25773. DOI

Oehlke A, Auer A A, Jahre I, Walfort B, Rüffer T, Zoufalá P, Lang H, Spange S. J Org Chem. 2007;72:4328–4339. doi: 10.1021/jo070084v. PubMed DOI

Ren Y, Yu X-Q, Zhang D-J, Wang D, Zhang M-L, Xu G-B, Zhao X, Tian Y-P, Shao Z-S, Jiang M-H. J Mater Chem. 2002;12:3431–3437. doi: 10.1039/b206578a. DOI

Liu Z-q, Fang Q, Wang D, Cao D-x, Xue G, Yu W-t, Lei H. Chem–Eur J. 2003;9:5074–5084. doi: 10.1002/chem.200304833. PubMed DOI

Perttu E K, Arnold M, Iovine P M. Tetrahedron Lett. 2005;46:8753–8756. doi: 10.1016/j.tetlet.2005.10.033. DOI

Rodriguez J G, Esquivias J, Lafuente A, Rubio L. Tetrahedron. 2006;62:3112–3122. doi: 10.1016/j.tet.2006.01.032. DOI

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