Art

J-GLOBAL ID：202002278566378489   Reference number：20A0539973

TRIALKYLSULFONIUM AND TETRAALKYLAMMONIUM SALTS AS HYDROGEN-BONDING CATALYSTS IN AN AZA-DIELS-ALDER REACTION: EXPERIMENTAL AND COMPUTATIONAL STUDIES

アザ-Diels-Alder反応における水素結合触媒としてのトリアルキルスルホニウムおよびテトラアルキルアンモニウム塩:実験的および計算的研究

Author (5)： YAMANAKA Masahiro (Rikkyo Univ., Tokyo, JPN) ,  MOCHIZUKI Ayaka (Rikkyo Univ., Tokyo, JPN) ,  NAKAMURA Takumi (Nagasaki Univ., Nagasaki, JPN) ,  MARUOKA Keiji (Kyoto Univ., Kyoto, JPN) ,  SHIRAKAWA Seiji (Nagasaki Univ., Nagasaki, JPN)
Material： Heterocycles  (International Journal for Reviews and Communications in Heterocyclic Chemistry)
Volume： 101  Issue： 2  Page： 580-592  Publication year： Jan. 01, 2020 
JST Material Number： S0966A  ISSN： 0385-5414  CODEN： HTCYAM  Document type： Article
Article type： 原著論文  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： *Diels-Alder reaction ,  nitrogen heterocyclic compound ,  *sulfonium ,  quaternary ammonium ,  hydrogen-bonded complex ,  intramolecular hydrogen bond ,  sulfur heterocyclic compound ,  onium compound ,  counter-ion ,  counter ion effect ,  density functional method ,  borate ,  acid dissociation constant ,  aromatic amine ,  aromatic aldehyde ,  azomethine
Semi thesaurus term： *aza-Diels-Alder reaction ,  DFT calculation ,  pKa ,  Borates

JST classification (5)： Cyclization reaction,ring-opening reaction  (CF02050I) ,  Aliphatic sulfoxides,sulfones,sulfonium compounds  (CF03150Y) ,  Aliphatic amines,imines,quaternary ammonium,immonium compounds  (CF03070L) ,  Nitrogen heterocycles in general  (CF07040G) ,  Sulfur heterocycles in general  (CF07030V)

Substance index (17)： Mepiquat ,  1,1-ジメチルピペリジニウム・テトラキス[3,5-ビス(トリフルオロメチル)フェニル]ボラート ,  1,1-ジメチルピペリジニウム・ヨージド ,  1-(4-Methoxyphenyl)-2-phenyl-2,3-dihydro-4(1H)-pyridone ,  1,2-Diphenyl-2,3-dihydro-4(1H)-pyridone ,  1-(4-Chlorophenyl)-2-phenyl-2,3-dihydro-4(1H)-pyridone ,  1-Phenyl-2-(2-furyl)-1,2-dihydropyridine-4(3H)-one ,  1,2-Dihydro-2-(4-methoxyphenyl)-1-phenyl-4(3H)-pyridinone ,  1-Phenyl-2-(biphenyl-4-yl)-1,2-dihydropyridine-4(3H)-one ,  2-[4-(methylsulfanyl)phenyl]-1-phenyl-2,3-dihydropyridin-4-one ,  1-Methylhexahydrothiopyrylium ,  1-メチルヘキサヒドロチオピリリウム・テトラキス[3,5-ビス(トリフルオロメチル)フェニル]ボラート ,  1-メチルヘキサヒドロチオピリリウム・ヨージド ,  3-(Trimethylsiloxy)-1-methoxy-1,3-butadiene ,  Benzyltrimethylammonium ,  N-Phenylbenzenemethanimine ,  Benzyldimethylsulfonium

Reference (10)：

• (a) G. A. Olah, Aldrichimica Acta, 1973, 6, 7; (b) E. Vedejs and F. G. West, Chem. Rev., 1986, 86, 941; (c) G. K. S. Prakash, J. Org. Chem., 2006, 71, 3661; (d) Recent Developments in Carbocation and Onium Ion Chemistry, ed. by K. K. Laali, American Chemical Society, Washington DC, 2007 (ACS Symposium Series 965); (e) J. B. Sweeney, Chem. Soc. Rev., 2009, 38, 1027; (f) X. Guo and W. Hu, Acc. Chem. Res., 2013, 46, 2427; (g) S. Preshlock, M. Tredwell, and V. Gouverneur, Chem. Rev., 2016, 116, 719.
• (a) E. V. Dehmlow and S. S. Dehmlow, Phase Transfer Catalysis, VCH, Weinheim, 1993; (b) C. M. Starks, C. L. Liotta, and M. Halpern, Phase-Transfer Catalysis, Chapman & Hall, New York, 1994; (c) Handbook of Phase-Transfer Catalysis, ed. by Y. Sasson and R. Neumann, Blackie Academic & Professional, London, 1997; (d) Phase-Transfer Catalysis, ed. by M. E. Halpern, American Chemical Society, Washington DC, 1997 (ACS Symposium Series 659); (e) M. J. O'Donnell, Aldrichimica Acta, 2001, 34, 3; (f) T. Ooi and K. Maruoka, Acc. Chem. Res., 2004, 37, 526; (g) T. Ooi and K. Maruoka, Angew. Chem. Int. Ed., 2007, 46, 4222; (h) Asymmetric Phase-Transfer Catalysis, ed. by K. Maruoka, Wiley-VCH, Weinheim, 2008; (i) S.-s. Jew and H.-g. Park, Chem. Commun., 2009, 7090; (j) T. Werner, Adv. Synth. Catal., 2009, 351, 1469; (k) D. Enders and T. V. Nguyen, Org. Biomol. Chem., 2012, 10, 5327; (l) J. Novacek and M. Waser, Eur. J. Org. Chem., 2013, 637; (m) S. Shirakawa and K. Maruoka, Angew. Chem. Int. Ed., 2013, 52, 4312; (n) S. Kaneko, Y. Kumatabara, and S. Shirakawa, Org. Biomol. Chem., 2016, 14, 5367; (o) S. Liu, Y. Kumatabara, and S. Shirakawa, Green Chem., 2016, 18, 331.
• (a) S. Shirakawa, S. Liu, S. Kaneko, Y. Kumatabara, A. Fukuda, Y. Omagari, and K. Maruoka, Angew. Chem. Int. Ed., 2015, 54, 15767; (b) Y. Kumatabara, S. Kaneko, S. Nakata, S. Shirakawa, and K. Maruoka, Chem. Asian J., 2016, 11, 2126; (c) S. Kaneko, Y. Kumatabara, S. Shimizu, K. Maruoka, and S. Shirakawa, Chem. Commun., 2017, 53, 119.
• (a) M. T. Reetz, Angew. Chem., Int. Ed. Engl., 1988, 27, 994; (b) M. T. Reetz, S. Hütte, and R. Goddard, J. Am. Chem. Soc., 1993, 115, 9339; (c) M. T. Reetz, S. Hütte, and R. Goddard, J. Phys. Org. Chem., 1995, 8, 231; (d) M. T. Reetz, S. Hütte, R. Goddard, and C. Robyr, Chem. Eur. J., 1996, 2, 382; (e) M. T. Reetz, S. Hütte, and R. Goddard, J. Prakt. Chem., 1999, 341, 297; (f) R. Goddard, H. M. Herzog, and M. T. Reetz, Tetrahedron, 2002, 58, 7847; (g) C. E. Cannizzaro and K. N. Houk, J. Am. Chem. Soc., 2002, 124, 7163; (h) T. Ohshima, T. Shibuguchi, Y. Fukuta, and M. Shibasaki, Tetrahedron, 2004, 60, 7743; (i) Y. Park, E. Park, H. Jung, Y.-J. Lee, S.-s. Jew, and H.-g. Park, Tetrahedron, 2011, 67, 1166; (j) T. C. Cook, M. B. Andrus, and D. H. Ess, Org. Lett., 2012, 14, 5836; (k) C. Thomas, A. Milet, F. Peruch, and B. Bibal, Polym. Chem., 2013, 4, 3491; (l) C. Thomas, S. Brut, and B. Bibal, Tetrahedron, 2014, 70, 1646; (m) T. Kamachi and K. Yoshizawa, Org. Lett., 2014, 16, 472; (n) C. P. Johnston, A. Kothari, T. Sergeieva, S. I. Okovytyy, K. E. Jackson, R. S. Paton, and M. D. Smith, Nat. Chem., 2015, 7, 171; (o) Q. Peng and R. S. Paton, Acc. Chem. Res., 2016, 49, 1042; (p) J. Novacek, J. A. Izzo, M. J. Vetticatt, and M. Waser, Chem. Eur. J., 2016, 22, 17339; (q) P. Nagorny and Z. Sun, Beilstein J. Org. Chem., 2016, 12, 2834.
• (a) Y. Yuan, X. Li, and K. Ding, Org. Lett., 2002, 4, 3309; (b) C. Loncaric, K. Manabe, and S. Kobayashi, Chem. Commun., 2003, 574; (c) Y. Takeda, D. Hisakuni, C.-H. Lin, and S. Minakata, Org. Lett., 2015, 17, 318; (d) M. Kaasik, A. Metsala, S. Kaabel, K. Kriis, I. Järving, and T. Kanger, J. Org. Chem., 2019, 84, 4294; (e) J. Kollmann, Y. Zhang, W. Schilling, T. Zhang, D. Riemer, and S. Das, Green Chem., 2019, 21, 1916.

Terms in the title (7)： アザ-Diels-Alder反応 ,  水素結合 ,  触媒 ,  塩 ,  実験 ,  計算 ,  研究