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Pure Appl. Chem., 1999, Vol. 71, No. 8, pp. 1435-1442

http://dx.doi.org/10.1351/pac199971081435

Palladium-catalyzed annulation

R. C. Larock

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  • Xie Zheng, Wu Pan, Cai Liangzhen, Tong Xiaofeng: Palladium-catalyzed cyclization of vinyl iodide-tethered allensulfonamide. Tetrahedron Letters 2014, 55, 2160. <http://dx.doi.org/10.1016/j.tetlet.2014.02.087>
  • Che Chao, Yang Bo, Jiang Xianlong, Shao Taofeng, Yu Zhixiong, Tao Chuanye, Li Song, Lin Shuo: Syntheses of Fused Tetracyclic Quinolines via Ugi-Variant MCR and Pd-Catalyzed Bis-annulation. J. Org. Chem. 2014, 79, 436. <http://dx.doi.org/10.1021/jo4024792>
  • Le Bras Jean, Muzart Jacques: Palladium-catalysed inter- and intramolecular formation of C–O bonds from allenes. Chem. Soc. Rev. 2014, 43, 3003. <http://dx.doi.org/10.1039/c3cs60379b>
  • Lechel Tilman, Pfrengle Fabian, Reissig Hans-Ulrich, Zimmer Reinhold: Three Carbons for Complexity! Recent Developments of Palladium-Catalyzed Reactions of Allenes. ChemCatChem 2013, 5, 2100. <http://dx.doi.org/10.1002/cctc.201200875>
  • Prakash Praveen, Jijy Eliyan, Preethanuj Preethalayam, Pihko Petri M., Sarath Chand Sarngadharan, Radhakrishnan Kokkuvayil V.: Palladium-Catalyzed Skeletal Rearrangement of Spirotricyclic Olefins: A Facile One-Pot Strategy for the Synthesis of a Novel Motif with Cyclopentene Fused to Benzofuran and Pyrazolidine. Chem. Eur. J. 2013, 19, 10473. <http://dx.doi.org/10.1002/chem.201301475>
  • John Jubi, Rajan Rani, Sarath Chand S., Prakash Praveen, Joseph Nayana, Suresh Eringathodi, Radhakrishnan K.V.: Palladium catalyzed reaction of ortho-functionalized aryl iodides with bicyclic hydrazines: facile route toward heteroannulated cyclopentenes and azabicycles. Tetrahedron 2013, 69, 152. <http://dx.doi.org/10.1016/j.tet.2012.10.053>
  • Tyaglivy Alexander S., Gulevskaya Anna V., Pozharskii Alexander F., Askalepova Olga I.: Nucleophilic cyclization of 3-alkynylquinoxaline-2-carbonitriles into pyrido[3,4-b]quinoxalines. Tetrahedron 2013, 69, 9804. <http://dx.doi.org/10.1016/j.tet.2013.09.005>
  • Bej Ansuman, Chakraborty Amarnath, Sarkar Amitabha: Solvent free, phosphine free Pd-catalyzed annulations of aryl bromides with diarylacetylenes. RSC Adv. 2013, 3, 15812. <http://dx.doi.org/10.1039/c3ra41924j>
  • Gulevskaya A. V., Tyaglivy A. S.: Nucleophilic cyclizations of enediynes as a method for polynuclear heterocycle synthesis. Chem Heterocycl Compd 2012, 48, 82. <http://dx.doi.org/10.1007/s10593-012-0972-8>
  • Gulevskaya Anna V., Nguyen Huong T.L., Tyaglivy Alexander S., Pozharskii Alexander F.: New insight into anionic cyclizations of alkynyl- and ortho-dialkynylarenes: a specific reactivity of 3-alkynyl-2-chloro- and 2,3-dialkynylquinoxalines and related compounds toward CH-acids’ carbanions. Tedrahedron 2012, 68, 488. <http://dx.doi.org/10.1016/j.tet.2011.11.018>
  • Okuro Kazumi, Alper Howard: Palladium-Catalyzed Intermolecular Cyclocarbonylation of 2-Iodoanilines with the Michael Acceptor, Diethyl Ethoxycarbonylbutendienoate. J Org Chern 2012, 77, 4420. <http://dx.doi.org/10.1021/jo300173g>
  • Shukla Satya Prakash, Tiwari Rakesh K., Verma Akhilesh K.: Palladium-Catalyzed Sonogashira-Coupling Conjoined C–H Activation: A Regioselective Tandem Strategy to Access Indolo- and Pyrrolo[1,2-a]quinolines. J. Org. Chem. 2012, 77, 10382. <http://dx.doi.org/10.1021/jo302112a>
  • Wang Ruiping, Mo Song, Lu Yongzhong, Shen Zengming: Domino Sonogashira Coupling/Cyclization Reaction Catalyzed by Copper and ppb Levels of Palladium: A Concise Route to Indoles and Benzo[b]furans. Synth Catal 2011, 353, 713. <http://dx.doi.org/10.1002/adsc.201000730>
  • Joseph Nayana, John Jubi, Rajan Rani, Thulasi Sreeja, Mohan Anupa, Suresh E., Radhakrishnan K.V.: Transition metal catalyzed carboannulation of diazabicyclic alkenes with ambiphilic bifunctional reagents: a facile route towards functionalized indanones and indanols. Tetrahedron 2011, 67, 4905. <http://dx.doi.org/10.1016/j.tet.2011.04.087>
  • Huang Xian, Sha Feng, Tong Jiawei: Facile and Efficient Synthesis of Hydrophenanthren-1(2H)-ones and Naphtho[2,1-c]furan-3(1H)-ones by a Palladium-Catalyzed Aryne Annulation Strategy. Adv Synth Catal 2010, 352, 379. <http://dx.doi.org/10.1002/adsc.200900703>
  • Vicente José, Abad José-Antonio, López-Sáez María-José, Jones Peter G., Bautista Delia: Reactivity of ortho-Substituted Aryl–Palladium Complexes towards Carbodiimides, Isothiocyanates, Nitriles, and Cyanamides. Chem Eur J 2010, 16, 661. <http://dx.doi.org/10.1002/chem.200901828>
  • Larock Richard C.: ChemInform Abstract: Palladium-Catalyzed Annulation. ChemInform 2010, 31, no. <http://dx.doi.org/10.1002/chin.200025302>
  • Zhang Xiaoxia, Larock Richard C.: Synthesis of highly substituted 1,3-dienes, 1,3,5-trienes, and 3,6-disubstituted cyclohexenes by the palladium-catalyzed coupling of organic halides, internal alkynes or 1,3-cyclohexadienes, and organoboranes. Tetrahedron 2010, 66, 4265. <http://dx.doi.org/10.1016/j.tet.2010.03.119>
  • Wang Congyang, Rakshit Souvik, Glorius Frank: Palladium-Catalyzed Intermolecular Decarboxylative Coupling of 2-Phenylbenzoic Acids with Alkynes via C−H and C−C Bond Activation. J Am Chem Soc 2010, 132, 14006. <http://dx.doi.org/10.1021/ja106130r>
  • Hu Yanhe, Liu Jing, Lü Zhixin, Luo Xiancai, Zhang Heng, Lan Yu, Lei Aiwen: Base-Induced Mechanistic Variation in Palladium-Catalyzed Carbonylation of Aryl Iodides. J Am Chem Soc 2010, 132, 3153. <http://dx.doi.org/10.1021/ja909962f>
  • Chernyak Natalia, Gevorgyan Vladimir: Synthesis of Fluorenes via the Palladium-Catalyzed 5-exo-dig Annulation of o-Alkynylbiaryls. Adv Synth Catal 2009, 351, 1101. <http://dx.doi.org/10.1002/adsc.200800765>
  • Obushak Mykola D., Matiychuk Vasyl S., Turytsya Victor V.: A new approach to the synthesis of 3,4-dihydroisocoumarin derivatives. Tetrahetron Lett 2009, 50, 6112. <http://dx.doi.org/10.1016/j.tetlet.2009.08.024>
  • John Jubi, U. Indu, Suresh Eringathodi, Radhakrishnan K. V.: Palladium Catalyzed Tandem Ring Opening−Ring Closing Reaction of Diazabicyclic Alkenes: A Facile One Pot Strategy for Cyclopentannulation of Heterocycles. J Am Chem Soc 2009, 131, 5042. <http://dx.doi.org/10.1021/ja900477e>
  • Ye Deju, Wang Jinfang, Zhang Xu, Zhou Yu, Ding Xiao, Feng Enguang, Sun Haifeng, Liu Guannan, Jiang Hualiang, Liu Hong: Gold-catalyzed intramolecular hydroamination of terminal alkynes in aqueous media: efficient and regioselective synthesis of indole-1-carboxamides. Green Chem 2009, 11, 1201. <http://dx.doi.org/10.1039/b904044g>
  • Guo Li-Na, Duan Xin-Hua, Hu Jie, Bi Hai-Peng, Liu Xue-Yuan, Liang Yong-Min: Synthesis of Indene and Naphthalene Derivatives by a Palladium-Catalyzed Domino Carbopalladation/Cyclization/Coupling Process. Eur J Org Chem 2008, 2008, 1418. <http://dx.doi.org/10.1002/ejoc.200701043>
  • Liu Zhijian, Larock Richard C.: Palladium-Catalyzed, Sequential, Three-Component Cross-Coupling of Aryl Halides, Alkynes, and Arynes. Angew Chem 2007, 119, 2587. <http://dx.doi.org/10.1002/ange.200604969>
  • Liu Zhijian, Larock Richard C.: Palladium-Catalyzed, Sequential, Three-Component Cross-Coupling of Aryl Halides, Alkynes, and Arynes. Angew Chem Int Ed 2007, 46, 2535. <http://dx.doi.org/10.1002/anie.200604969>
  • Venkataraman Subramanian, Barange Deepak Kumar, Pal Manojit: One-pot synthesis of 2-substituted furo[3,2-c]quinolines via tandem coupling–cyclization under Pd/C-copper catalysis. Tetrahetron Lett 2006, 47, 7317. <http://dx.doi.org/10.1016/j.tetlet.2006.08.025>
  • Dang Shi, Gulevskaya A. V., Pozharskii A. F., Kotelevskaya R. V.: Purins, pyrimidines, and related condensed systems. 22. Synthesis and heterocyclization of 7-alkynyl- and 6,7-dialkynyllumazines. Chem Heterocycl Compd 2005, 41, 124. <http://dx.doi.org/10.1007/s10593-005-0118-3>
  • Esho Noor, Desaulniers Jean-Paul, Davies Brian, Chui Helen M.-P., Rao Meneni Srinivasa, Chow Christine S., Szafert Slawomir, Dembinski Roman: NMR conformational analysis of p-tolyl furanopyrimidine 2′-deoxyribonucleoside and crystal structure of its 3′,5′-di-O-acetyl derivative. biorg med chem 2005, 13, 1231. <http://dx.doi.org/10.1016/j.bmc.2004.11.013>
  • Inamoto Kiyofumi, Yamamoto Akio, Ohsawa Kazutoshi, Hiroya Kou, Sakamoto Takao: Highly Regioselective Palladium-Catalyzed Annulation Reactions of Heteroatom-Substituted Allenes for Synthesis of Condensed Heterocycles. Chem Pharm Bull 2005, 53, 1502. <http://dx.doi.org/10.1248/cpb.53.1502>
  • Hong Ki Bum, Lee Chul Wee, Yum Eul Kgun: Synthesis of 2-substituted indoles by palladium-catalyzed heteroannulation with Pd–NaY zeolite catalysts. Tetrahetron Lett 2004, 45, 693. <http://dx.doi.org/10.1016/j.tetlet.2003.11.075>
  • Hopkins Corey R., Collar Nicola: 6-Substituted-5H-pyrrolo[2,3-b]pyrazines via palladium-catalyzed heteroannulation from N-(3-chloropyrazin-2-yl)-methanesulfonamide and alkynes. Tetrahetron Lett 2004, 45, 8087. <http://dx.doi.org/10.1016/j.tetlet.2004.08.155>
  • Kato Fumiko, Hiroi Kunio: Stereochemistry of the Asymmetric Carbopalladation of Allenes Followed by Nucleophilic Substitution Reactions with Carbo- and Aminonucleophiles. Chem Pharm Bull 2004, 52, 95. <http://dx.doi.org/10.1248/cpb.52.95>
  • Synthesis of Tetracyclic 5-Azaindole Analogues by Palladium-Catalyzed Sequential Annulation. Bulletin of the Korean Chemical Society 2004, 25, 1351. <http://dx.doi.org/10.5012/bkcs.2004.25.9.1351>
  • Kadnikov Dmitry V, Larock Richard C: Palladium-catalyzed carbonylative annulation of terminal alkynes: synthesis of coumarins and 2-quinolones. J Organomet Chem 2003, 687, 425. <http://dx.doi.org/10.1016/S0022-328X(03)00786-1>
  • de Koning Charles B., Rousseau Amanda L., van Otterlo Willem A.L.: Modern methods for the synthesis of substituted naphthalenes. Tetrahedron 2003, 59, 7. <http://dx.doi.org/10.1016/S0040-4020(02)01424-2>
  • Rozhkov Roman V., Larock Richard C.: Synthesis of Dihydrofurocoumarins via Palladium-Catalyzed Annulation of 1,3-Dienes by o-Iodoacetoxycoumarins. Org Lett 2003, 5, 797. <http://dx.doi.org/10.1021/ol027342p>
  • Synthesis of Pyrrolo[2,3-b]quinolines by Palladium-catalyzed Heteroannulation. Bulletin of the Korean Chemical Society 2003, 24, 1193. <http://dx.doi.org/10.5012/bkcs.2003.24.8.1193>
  • Teplý Filip, Stará Irena G., Starý Ivo, Kollárovič Adrian, Šaman David, Fiedler Pavel: Transition metal control in the reaction of alkyne-substituted phenyl iodides with terminal alkynes: Sonogashira coupling vs cyclic carbopalladation. Tetrahedron 2002, 58, 9007. <http://dx.doi.org/10.1016/S0040-4020(02)01154-7>
  • Tian Qingping, Larock Richard C.: Synthesis of 9-Alkylidene-9H-fluorenes by a Novel Palladium-Catalyzed Rearrangement. Org Lett 2000, 2, 3329. <http://dx.doi.org/10.1021/ol000220h>