Synthesis of novel photochromic pyrans via palladium-mediated reactions

Scholarly Works

• Korzhenko, K. S.; Yushkova, A. S.; Osipov, D. V.; Rashchepkina, D. A.; Demidov, O. P.; Osyanin, V. A. Divergent Transformations of 2-Nitro-1H-benzo[f]chromenes in Reactions with Alkylidenemalononitriles: Access to Naphtho[2,1-b]furans via Base-Mediated Pyran Ring Contraction. Organic letters 2024, 26, 1310–1315. doi:10.1021/acs.orglett.3c03879
• Fernandes, R. A.; Khatun, G. N.; Moharana, S. Chiral Pool Synthesis: Starting From Terpenes. Comprehensive Chirality; Elsevier, 2024; pp 542–580. doi:10.1016/b978-0-32-390644-9.00068-8
• Hu, L.; Rawal, V. H. Total Synthesis of the Chlorinated Pentacyclic Indole Alkaloid (+)-Ambiguine G. Journal of the American Chemical Society 2021, 143, 10872–10875. doi:10.1021/jacs.1c05762
• Aiken, S.; de Azevedo, O. D. C. C.; Chauhan, K.; Driscoll, T.; Elliott, P. I. P.; Gabbutt, C. D.; Heron, B. M. Base-Mediated Ring-Contraction of Pyran Systems Promoted by Palladium and Phase-Transfer Catalysis. The Journal of organic chemistry 2020, 85, 952–966. doi:10.1021/acs.joc.9b02901
• Tanaka, K.; Kishimoto, M.; Asada, Y.; Tanaka, Y.; Hoshino, Y.; Honda, K. Access to Electron-Deficient 2,2-Disubstituted Chromanes: A Highly Regioselective One-Pot Synthesis via an Inverse-Electron-Demand [4 + 2] Cycloaddition of ortho-Quinone Methides. The Journal of organic chemistry 2019, 84, 13858–13870. doi:10.1021/acs.joc.9b02036
• Strudwick, B. H.; O’Bryen, C.; Sanders, H. J.; Woutersen, S.; Buma, W. J. Opening 2,2-diphenyl-2H-chromene to infrared light. Physical chemistry chemical physics : PCCP 2019, 21, 11689–11696. doi:10.1039/c9cp01906e
• Dahms, B.; Kohlpaintner, P. J.; Wiebe, A.; Breinbauer, R.; Schollmeyer, D.; Waldvogel, S. R. Selective Formation of 4,4′-Biphenols by Anodic Dehydrogenative Cross- and Homo-Coupling Reaction. Chemistry (Weinheim an der Bergstrasse, Germany) 2019, 25, 2713–2716. doi:10.1002/chem.201805737
• Honda, K.; Tanaka, K.; Sukekawa, M.; Hoshino, Y.; Kishimoto, M. CsF-Promoted Desilylation and Ring-Contraction Reaction of Electron-Deficient 3-Silyl-2H-chromenes to 2-Benzylbenzofurans. HETEROCYCLES 2019, 99, 145–170. doi:10.3987/com-18-s(f)5
• Tanaka, K.; Hoshino, Y.; Honda, K. Development of regioselective inverse-electron-demand [4+2] cycloaddition with electron-rich arylalkynes for access to multi-substituted condensed oxapolycyclic compounds. Journal of Synthetic Organic Chemistry, Japan 2018, 76, 1341–1351. doi:10.5059/yukigoseikyokaishi.76.1341
• Tanaka, K.; Sukekawa, M.; Hoshino, Y.; Honda, K. The Ring-contraction Reaction of Electron-deficient 3-Silylchromene to 2-Benzylbenzofuran under Mildly Basic Conditions. Chemistry Letters 2018, 47, 440–443. doi:10.1246/cl.171124
• Sahoo, P. R.; Prakash, K.; Kumar, S. Experimental and theoretical investigations of cyanide detection using a photochromic naphthopyran. Supramolecular Chemistry 2016, 29, 192. doi:10.1080/10610278.2016.1197398
• Arai, K.; Kobayashi, Y.; Abe, J. Rational molecular designs for drastic acceleration of the color-fading speed of photochromic naphthopyrans. Chemical communications (Cambridge, England) 2015, 51, 3057–3060. doi:10.1039/c4cc10294k
• Cigáň, M.; Gáplovský, M.; Jakusová, K.; Donovalová, J.; Horváth, M.; Filo, J.; Gáplovský, A. Isatin N2-diphenylhydrazones: new easily synthesized Vis-Vis molecular photoswitches. RSC Advances 2015, 5, 62449–62459. doi:10.1039/c5ra06625e
• Morán-Poladura, P.; Rubio, E.; González, J. M. Gold(I)-catalyzed hydroarylation reaction of aryl (3-iodoprop-2-yn-1-yl) ethers: synthesis of 3-iodo-2H-chromene derivatives. Beilstein journal of organic chemistry 2013, 9, 2120–2128. doi:10.3762/bjoc.9.249
• Blackwell, C. J.; Gabbutt, C. D.; Guthrie, J. T.; Heron, B. M. The synthesis and properties of vinyl substituted naphthopyrans and their styrene copolymers. Dyes and Pigments 2012, 95, 408–420. doi:10.1016/j.dyepig.2012.05.017
• Regner, N.; Herzog, T. T.; Haiser, K.; Hoppmann, C.; Beyermann, M.; Sauermann, J.; Engelhard, M.; Cordes, T.; Rück-Braun, K.; Zinth, W. Light-switchable hemithioindigo-hemistilbene-containing peptides: ultrafast spectroscopy of the Z → E isomerization of the chromophore and the structural dynamics of the peptide moiety. The journal of physical chemistry. B 2012, 116, 4181–4191. doi:10.1021/jp300982a
• Gabbutt, C. D.; Heron, B. M.; Kilner, C. A.; Kolla, S. B. The synthesis and photochromism of a 2,2-diaryl-6-styryl-2H-[1]benzopyran: Unexpected palladium-mediated ring-contraction of a 6-bromo-2,2-diaryl-2H-[1]benzopyran. Dyes and Pigments 2012, 92, 825–830. doi:10.1016/j.dyepig.2011.05.005
• Sousa, C. M.; Pina, J.; de Melo, J. S.; Berthet, J.; Delbaere, S.; Coelho, P. J. Preventing the formation of the long-lived colored transoid-trans photoisomer in photochromic benzopyrans. Organic letters 2011, 13, 4040–4043. doi:10.1021/ol201549v
• Tulyakova, E. V.; Fedorova, O. A.; Micheau, J.-C.; Paramonov, S. V.; Lokshin, V.; Vermeersch, G.; Delbaere, S. Photochromism and metal complexation of a macrocyclic styryl naphthopyran. Chemphyschem : a European journal of chemical physics and physical chemistry 2011, 12, 1294–1301. doi:10.1002/cphc.201100052
• Terrett, N. Combinatorial Chemistry Online. Combinatorial Chemistry - an Online Journal 2009, 11, 33–36. doi:10.1016/j.comche.2009.08.001

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