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Interrupted Carbonyl‐Alkyne Metathesis

dc.contributor.authorMcFarlin, Austin T.
dc.contributor.authorWatson, Rebecca B.
dc.contributor.authorZehnder, Troy E.
dc.contributor.authorSchindler, Corinna S.
dc.date.accessioned2020-02-05T15:07:11Z
dc.date.availableWITHHELD_12_MONTHS
dc.date.available2020-02-05T15:07:11Z
dc.date.issued2020-01-23
dc.identifier.citationMcFarlin, Austin T.; Watson, Rebecca B.; Zehnder, Troy E.; Schindler, Corinna S. (2020). "Interrupted Carbonyl‐Alkyne Metathesis." Advanced Synthesis & Catalysis 362(2): 365-369.
dc.identifier.issn1615-4150
dc.identifier.issn1615-4169
dc.identifier.urihttps://hdl.handle.net/2027.42/153682
dc.description.abstractCarbonyl‐olefin metathesis and carbonyl‐alkyne metathesis represent established reactivity modes between carbonyls, alkenes, and alkynes under Lewis and Brønsted acid catalysis. Recently, an interrupted carbonyl‐olefin metathesis reaction has been reported that results in tetrahydrofluorenes via a distinct fragmentation of the reactive intermediate. We herein report the development of an analogous transformation interrupting the carbonyl‐alkyne metathesis reaction path resulting in dihydrofluorene products relying on Lewis acidic superelectrophiles as active catalytic species.
dc.publisherWiley-VCH
dc.subject.otherNazarov cyclization
dc.subject.othercarbonyl-alkyne metathesis
dc.subject.otherinterrupted carbonyl-alkyne metathesis
dc.subject.othersuperelectrophile
dc.subject.otherLewis acid catalysis
dc.titleInterrupted Carbonyl‐Alkyne Metathesis
dc.typeArticle
dc.rights.robotsIndexNoFollow
dc.subject.hlbsecondlevelChemistry
dc.subject.hlbtoplevelScience
dc.description.peerreviewedPeer Reviewed
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/153682/1/adsc201901358.pdf
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/153682/2/adsc201901358_am.pdf
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/153682/3/adsc201901358-sup-0001-misc_information.pdf
dc.identifier.doi10.1002/adsc.201901358
dc.identifier.sourceAdvanced Synthesis & Catalysis
dc.identifier.citedreferenceK. Kumari, D. S. Raghuvanshi, K. N. Singh, Tetrahedron 2013, 69, 82 – 88;
dc.identifier.citedreferenceA. Saito, J. Kasai, T. Konishi, Y. Hanzawa, J. Org. Chem. 2010, 75, 6980 – 6982;
dc.identifier.citedreferenceJ. D. Cuthbertson, A. A. Godfrey, R. J. K. Taylor, Org. Lett. 2011, 13, 3976 – 3979;
dc.identifier.citedreferenceM.-N. Lin, S.-H. Wu, M.-C. P. Yeh, Adv. Synth. Catal. 2011, 353, 3290 – 3294;
dc.identifier.citedreferenceL. Liu, B. Xu, G. B. Hammond, Beilstein J. Org. Chem. 2011, 7, 606 – 614;
dc.identifier.citedreferenceC. González-Rodríguez, L. Escalante, J. A. Varela, L. Castedo, C. Saá, Org. Lett. 2009, 11, 1531 – 1533;
dc.identifier.citedreferenceM.-C. P. Yeh, M.-N. Lin, C.-H. Hsu, C.-J. Liang, J. Org. Chem. 2013, 78, 12381 – 12396;
dc.identifier.citedreferenceI. R. Siddiqui, Rahila, S. Shamim, P. Rai, Shireen, M. A. Waseem, A. A. H. Abumhdi, Tetrahedron Lett. 2013, 54, 6991 – 6994;
dc.identifier.citedreferenceM. Nayak, I. Kim, J. Org. Chem. 2015, 80, 11460 – 11467;
dc.identifier.citedreferenceY. Jung, I. Kim, J. Org. Chem. 2015, 80, 2001 – 2005;
dc.identifier.citedreferenceK. Ng, V. Tran, T. Minehan, Tetrahedron Lett. 2016, 57, 415 – 419;
dc.identifier.citedreferenceA. M. Garkhedkar, G. C. Senadi, J.-J. Wang, Org. Lett. 2017, 19, 488 – 491;
dc.identifier.citedreferenceK. Murai, K. Tateishi, A. Saito, Org. Biomol. Chem. 2016, 14, 10352 – 10356.
dc.identifier.citedreference 
dc.identifier.citedreferenceG. A. Olah, Angew. Chem. Int. Ed. Engl. 1993, 32, 767 – 788;
dc.identifier.citedreferenceG. A. Olah, D. A. Klumpp, in Superelectrophiles and Their Chemistry. Wiley-VCH, Verlag GmbH & Co. KGaA, 2007.
dc.identifier.citedreference 
dc.identifier.citedreferenceH. Albright, P. S. Riehl, C. C. McAtee, J. P. Reid, J. R. Ludwig, L. A. Karp, P. M. Zimmerman, M. S. Sigman, C. S. Schindler, J. Am. Chem. Soc. 2019, 141, 1690 – 1700;
dc.identifier.citedreferenceR. B. Watson, A. J. Davis, D. J. Nasrallah, J. L. Gomez-Lopez, C. S. Schindler, Chemrxiv 2019, DOI: 10.26434/chemrxiv.9911783.v1.
dc.identifier.citedreference 
dc.identifier.citedreferenceW. Beck, K. Sünkel, Chem. Rev. 1988, 88, 1405 – 1421;
dc.identifier.citedreferenceS. H. Strauss, Chem. Rev. 1993, 93, 927 – 942.
dc.identifier.citedreferenceH. Kinoshita, C. Miyama, K. Miura, Tetrahedron Lett. 2016, 57, 5065 – 5069.
dc.identifier.citedreferenceFor carbonyl-olefin metathesis reactions proceeding via oxetane photoadducts, see:
dc.identifier.citedreferenceG. Jones   II, S. B. Schwartz, M. T. Marton, J. Chem. Soc. Chem. Commun. 1973, 374 – 375;
dc.identifier.citedreferenceG. Jones   II, M. A. Acquadro, M. A. Carmody, J. Chem. Soc. Chem. Commun. 1975, 206 – 207;
dc.identifier.citedreferenceH. A. J. Carless, H. S. Trivedi, J. Chem. Soc. Chem. Commun. 1979, 382 – 383;
dc.identifier.citedreferenceM. D’Auria, R. Racioppi, L. Viggiani, Photochem. Photobiol. Sci. 2010, 9, 1134 – 1138;
dc.identifier.citedreferenceR. Pérez-Ruiz, S. Gil, M. A. Miranda, J. Org. Chem. 2005, 70, 1376 – 1381;
dc.identifier.citedreferenceR. Pérez-Ruiz, M. A. Miranda, R. Alle, K. Meerholz, A. G. Griesbeck, Photochem. Photobiol. Sci. 2006, 5, 51 – 55;
dc.identifier.citedreferenceR. A. Valiulin, A. G. Kutateladze, Org. Lett. 2009, 11, 3886 – 3889;
dc.identifier.citedreferenceR. A. Valiulin, T. M. Arisco, A. G. Kutateladze, J. Org. Chem. 2011, 76, 1319 – 1332;
dc.identifier.citedreferenceR. A. Valiulin, T. M. Arisco, A. G. Kutateladze, J. Org. Chem. 2013, 78, 2012 – 2025.
dc.identifier.citedreferenceSucceeding one-step synthetic protocols were driven by the development of molybdenum alkylidenes as reagents: G. C. Fu, R. H. Grubbs, J. Am. Chem. Soc. 1993, 115, 3800 – 3801.
dc.identifier.citedreferenceFor Brønsted and Lewis acid mediated carbonyl-olefin metathesis reactions, see:
dc.identifier.citedreferenceI. Schopov, C. Jossifov, Makromol. Chem. Rapid Commun. 1983, 4, 659 – 662;
dc.identifier.citedreferenceA. Soicke, N. Slavov, J.-M. Neudörfl, H.-G. Schmalz, Synlett 2011, 17, 2487 – 2490;
dc.identifier.citedreferenceH.-P. van Schaik, R.-J. Vijn, F. Bickelhaupt, Angew. Chem. Int. Ed. 1994, 33, 1611 – 1612;
dc.identifier.citedreferenceC. Jossifov, R. Kalinova, A. Demonceau, Chim. Oggi 2008, 26, 85 – 87.
dc.identifier.citedreferenceFor organocatalytic approaches, see:
dc.identifier.citedreferenceA. K. Griffith, C. M. Vanos, T. H. Lambert, J. Am. Chem. Soc. 2012, 134, 18581 – 18584;
dc.identifier.citedreferenceX. Hong, Y. Liang, A. K. Griffith, T. H. Lambert, K. N. Houk, Chem. Sci. 2014, 5, 471 – 475;
dc.identifier.citedreferenceY. Zhang, J. Jermaks, S. N. MacMillan, T. H. Lambert, ACS Catal. 2019, DOI: 10.1021/acscatal.9b03656.
dc.identifier.citedreferenceBrønsted-acid catalyzed carbonyl-olefin metathesis reactions were recently reported to proceed inside a supramolecular host:
dc.identifier.citedreferenceL. Catti, K. Tiefenbacher, Angew. Chem. Int. Ed. 2018, 57, 14589 – 14592;
dc.identifier.citedreferenceY. Zhu, J. Rebek   Jr, Y. Yu, Chem. Commun., 2019, 55, 3573 – 3577.
dc.identifier.citedreference 
dc.identifier.citedreferenceJ. R. Ludwig, P. M. Zimmerman, J. B. Gianino, C. S. Schindler, Nature 2016, 533, 374 – 379;
dc.identifier.citedreferenceC. M. McAtee, P. S. Riehl, C. S. Schindler, J. Am. Chem. Soc. 2017, 139, 2960 – 2963;
dc.identifier.citedreferenceE. J. Groso, A. N. Golonka, R. A. Harding, B. W. Alexander, T. M. Sodano, C. S. Schindler, ACS Catal. 2018, 8, 2006 – 201;
dc.identifier.citedreferenceP. S. Riehl, D. J. Nasrallah, C. S. Schindler, Chem. Sci. 2019, 10, 10267 – 10274;
dc.identifier.citedreferenceL. Ma, W. Li, H. Xi, X. Bai, E. Ma, X. Yan, Z. Li, Angew. Chem. Int. Ed. 2016, 55, 10410 – 10413;
dc.identifier.citedreferenceC. S. Hanson, M. C. Psaltakis, J. J. Cortes, J. J. Devery   III, J. Am. Chem. Soc. 2019, 141, 11870 – 11880.
dc.identifier.citedreferenceH. Albright, H. L. Vonesh, M. R. Becker, B. W. Alexander, J. R. Ludwig, R. A. Wiscons, C. S. Schindler, Org. Lett. 2018, 20, 4954 – 4958.
dc.identifier.citedreferenceU. P. N. Tran, G. Oss, M. Breugst, E. Detmar, D. P. Pace, K. Liyanto, T. V. Nguyen, ACS Catal. 2019, 9, 912 – 919.
dc.identifier.citedreferenceS. Ni, J. Franzén, Chem. Commun. 2018, 54, 12982 – 12985.
dc.identifier.citedreferenceU. P. N. Tran, G. Oss, D. P. Pace, J. Ho, T. V. Nguyen, Chem. Sci. 2018, 9, 5145 – 5151.
dc.identifier.citedreferenceJ. R. Ludwig, S. Phan, C. M. McAtee, P. M. Zimmerman, J. J. Devery   III, C. S. Schindler, J. Am. Chem. Soc. 2017, 139, 10832 – 10842.
dc.identifier.citedreferenceJ. R. Ludwig, R. B. Watson, D. J. Nasrallah, J. B. Gianino, P. M. Zimmerman, R. A. Wiscons, C. S. Schindler, Science 2018, 361, 1363 – 1369.
dc.identifier.citedreference 
dc.identifier.citedreferenceC. E. Harding, G. R. Stanford, Jr. J. Org. Chem. 1989, 54, 3054 – 3056;
dc.identifier.citedreferenceC. E. Harding, S. L. King, J. Org. Chem. 1992, 57, 883 – 886;
dc.identifier.citedreferenceM. F. Wempe, J. R. Grunwell, J. Org. Chem. 1995, 60, 2714 – 2720;
dc.identifier.citedreferenceJ. R. Rhee, M. J. Krische, Org. Lett. 2005, 7, 2493 – 2495;
dc.identifier.citedreferenceK. C. M. Kurtz, R. P. Hsung, Y. Zhang, Org. Lett. 2006, 8, 231 – 234;
dc.identifier.citedreferenceT. Jin, Y. Yamamoto, Org. Lett. 2007, 9, 5259 – 5262;
dc.identifier.citedreferenceK. Tanaka, K. Sasaki, K. Takeishi, M. Hirano, Eur. J. Org. Chem. 2007, 19, 5675 – 5685;
dc.identifier.citedreferenceA. Saito, M. Umakoshi, N. Yagyu, Y. Hanzawa, Org. Lett. 2008, 10, 1783 – 1785;
dc.identifier.citedreferenceA. Saito, J. Kasai, Y. Odaira, H. Fukaya, Y. Hanzawa, J. Org. Chem. 2009, 74, 6544 – 5647;
dc.owningcollnameInterdisciplinary and Peer-Reviewed


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