Synlett 2019; 30(10): 1125-1143
DOI: 10.1055/s-0037-1611735
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© Georg Thieme Verlag Stuttgart · New York

Controlled-Coupling of Quinone Monoacetals by New Activation Methods: Regioselective Synthesis of Phenol-Derived Compounds

Tohru Kamitanaka
a  Research Organization of Science and Technology, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan   Email: kita@ph.ritsumei.ac.jp
,
Koji Morimoto
a  Research Organization of Science and Technology, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan   Email: kita@ph.ritsumei.ac.jp
b  College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan
,
a  Research Organization of Science and Technology, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan   Email: kita@ph.ritsumei.ac.jp
b  College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan
,
a  Research Organization of Science and Technology, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan   Email: kita@ph.ritsumei.ac.jp
› Author Affiliations
This work was partially supported by Grants-in-Aid for Scientific Research (A) (JSPS KAKENHI Grant Number 24249001) from the Japan Society for the Promotion of Science (JSPS), a Grant-in-Aid for Scientific Research on Innovative Areas ‘Advanced Molecular Transformation by Organocatalysts’ (MEXT Grant Number 23105006) from The Ministry of Education, Culture, Sports, Science and Technology (MEXT), and the Ritsumeikan Global Innovation Research Organization (R-GIRO) project.
T.K. acknowledges Grant-in-Aid for Research Activity Start-up (16H07340) from JSPS. T.D. acknowledges Grant-in-Aid for Young Scientist (A) (24689002), Grant-in-Aid for Scientific Research (C) (16K08186), and Grant-in-Aid for Challenging Exploratory Research (26620036) from JSPS. K.M. also acknowledges support from the Grant-in-Aid for Young Scientists (B) (23790030 and 25860017) and Grant-in-Aid for Research Activity Start-up (21890280) from JSPS.
Further Information

Publication History

Received: 26 December 2018

Accepted after revision: 23 January 2019

Publication Date:
25 March 2019 (online)


Abstract

We have studied for a long time the reaction of quinone acetal type compounds, such as quinone monoacetals, quinone O,S-acetals, and iminoquinone monoacetals, and have reported the regioselective introduction of various nucleophiles. Quinone monoacetals show various types of reactivities toward nucleophiles due to their unique structures. In this study, we found that aromatic and alkene nucleophiles can be regioselectively introduced into the α-position of the carbonyl group on quinone monoacetals by specific activation of the acetal moiety. These reactions enabled the metal-free synthesis of highly functionalized aromatic compounds by the regioselective introduction of nucleophiles. In this account, we describe our recent studies of the coupling of quinone monoacetals.

1 Introduction

2 Regioselective Introduction of Aromatic Nucleophiles into α-Position of Carbonyl

2.1 Biaryl Synthesis by Introduction of Aromatic Nucleophiles

2.2 Synthesis of Terphenyls and Oligoarenes by Iterative Coupling

2.3 Synthesis of Phenol Cross-Coupling Products

3 [3+2] Coupling with Alkene Nucleophiles

3.1 Development of Efficient [3+2] Coupling

3.2 Improvement of Brønsted Acid Promotor

4 Synthesis of α-Aryl Carbonyl Compounds Triggered by Silyl Transfer

5 Utilization of o-Quinone Monoacetals

6 Application to Iminoquinone Monoacetals

7 Conclusion

 
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    • 38d Goto H, Katagiri H, Furusho Y, Yashima E. J. Am. Chem. Soc. 2006; 128: 7176
    • 38e Hayashi N, Yoshikawa T, Ohnuma T, Higuchi H, Sako K, Uekusa H. Org. Lett. 2007; 9: 5417
    • 38f Lin DW, Masuda T, Biskup MB, Nelson JD, Baran PS. J. Org. Chem. 2011; 76: 1013

    • A review:
    • 38g Adrio LA, Míguez JM. A, Hii KK. Org. Prep. Proced. Int. 2009; 41: 331

      Selected reviews and accounts:
    • 39a Furusho Y, Yashima E. Chem. Rec. 2007; 7: 1
    • 39b Baldini L, Casnati A, Sansone F, Ungaro R. Chem. Soc. Rev. 2007; 36: 254
    • 39c Nishikubo T, Kudo H. J. Photopolym. Sci. Technol. 2011; 24: 9
    • 39d For recent examples including the use of oligophenols and related compounds see
    • 39e Reihmann MH, Ritter H. Macromol. Chem. Phys. 2000; 201: 1593
    • 39f Turac E, Surme Y, Sahmetlioglu E, Varol R, Narin I, Toppare L. J. Appl. Polym. Sci. 2008; 110: 564
    • 39g Prokofieva A, Dechert S, Große C, Sheldrick GM, Meyer F. Chem. Eur. J. 2009; 15: 4994
    • 39h Kaya İ, Yılırım M, Aydın A, Şenol D. React. Funct. Polym. 2010; 70: 815
    • 39i Furusho Y, Miwa K, Asai R, Yashima E. Chem. Eur. J. 2011; 17: 13954
    • 39j Mora-Pale M, Kwon SJ, Linhardt RJ, Dordick JS. Free Radical Biol. Med. 2012; 52: 962

      Synthesis of well-defined phenol-based oligoarenes:
    • 40a Manabe K, Ishikawa S. Chem. Commun. 2008; 3829 ; and references cited therein
    • 40b Minato A, Suzuki K, Tamao K, Kumada M. J. Chem. Soc., Chem. Commun. 1984; 511
    • 40c Cheng W, Snieckus V. Tetrahedron Lett. 1987; 28: 5097
    • 40d Zhang J, Moore JS, Xu Z, Aguirre RA. J. Am. Chem. Soc. 1992; 114: 2273

      Importance of phenol cross-coupling products:
    • 41a Rappoport Z. The Chemistry of Phenols . Wiley; Chichester: 2003
    • 41b Malkowsky IM, Rommel CE, Wedeking K, Frchlich R, Bergander K, Nieger M, Quaiser C, Griesbach U, Pgtter H, Waldvogel SR. Eur. J. Org. Chem. 2006; 241
    • 41c Kirste A, Hayashi S, Schnakenburg G, Malkowsky IM, Stecker F, Fischer A, Fuchigami T, Waldvogel SR. Chem. Eur. J. 2011; 17: 14164

      General synthetic method of phenol cross-coupling products:
    • 42a Brunel JM. Chem. Rev. 2005; 105: 857
    • 42b Ashenhurst JA. Chem. Soc. Rev. 2010; 39: 540
    • 42c Wang H. Chirality 2010; 22: 827
    • 42d Wendlandt AE, Suess AM, Stahl SS. Angew. Chem. Int. Ed. 2011; 50: 11062 ; see also ref. 33d

      Direct C–H couplings:
    • 43a Satoh T, Kawamura Y, Miura M, Nomura M. Angew. Chem., Int. Ed. Engl. 1997; 36: 1740
    • 43b Satoh T, Kawamura Y, Miura M, Nomura M. Chem. Lett. 1998; 931
    • 43c Saito S, Kano T, Muto H, Nakadai M, Yamamoto H. J. Am. Chem. Soc. 1999; 121: 8943
    • 43d Bedford RB, Coles SJ, Hursthouse MB, Limmert ME. Angew. Chem. Int. Ed. 2003; 42: 112
    • 43e Bedford RB, Limmert ME. J. Org. Chem. 2003; 68: 8669
    • 43f Oi S, Watanabe S, Fukita S, Inoue Y. Tetrahedron Lett. 2003; 44: 8665
    • 43g Wetzel A, Pratsch G, Kolb R, Heinrich MR. Chem. Eur. J. 2010; 16: 2547

      Oxidative coupling of phenols:
    • 44a Egami H, Katsuki T. J. Am. Chem. Soc. 2009; 131: 6082
    • 44b Egami H, Matsumoto K, Oguma T, Kunisu T, Katsuki T. J. Am. Chem. Soc. 2010; 132: 13633
    • 44c Holtz-Mulholland M, de Leseleuc M, Collins SK. Chem. Commun. 2013; 49: 1835
    • 44d Lee YE, Cao T, Torruellas C, Kozlowski MC. J. Am. Chem. Soc. 2014; 136: 6782
    • 44e Elsler B, Schollmeyer D, Dyballa KM, Franke R, Waldvogel SR. Angew. Chem. Int. Ed. 2014; 53: 5210
    • 44f More NY, Jeganmohan M. Org. Lett. 2015; 17: 3042
    • 44g Libman A, Shalit H, Vainer Y, Narute S, Kozuch S, Pappo D. J. Am. Chem. Soc. 2015; 137: 11453
    • 44h Morimoto K, Sakamoto K, Ohshika T, Dohi T, Kita Y. Angew. Chem. Int. Ed. 2016; 55: 3652

      For early reports, see:
    • 45a Petrov AD, Sadykh-Zade SI, Filatova EI. Zh. Obshch. Khim. 1959; 29: 2936
    • 45b Baukov JI, Burlachenko GS, Lutsenko IF. J. Organomet. Chem. 1965; 3: 478
    • 45c Lutsenko IF, Baukor YI, Burlachenko GS, Khasapor BN. J. Organomet. Chem. 1966; 5: 20
    • 45d Arth GE, Poos GI, Lukes RM, Robinson FM, Johns WF, Feurer M, Sarett LH. J. Am. Chem. Soc. 1954; 76: 1715
    • 45e Arens JF. Recl. Trav. Chim. Pays-Bas 1955; 74: 769

      For selected reviews and accounts, see:
    • 46a Brownbridge P. Synthesis 1983; 1
    • 46b Brownbridge P. Synthesis 1983; 85
    • 46c Kuwajima I, Nakamura E. Acc. Chem. Res. 1985; 18: 181
    • 46d Carreira EM. In Comprehensive Asymmetric Catalysis I–III, Vol. 3. Jacobsen EN, Pfaltz A, Yamamoto H. Springer; New York: 1999: 997-1065
    • 46e Kobayashi S, Manabe K, Ishitani H, Matsuo J.-I. In Science of Synthesis, Vol. 4. Fleming I. Thieme; Stuttgart: 2002: 317-369
    • 46f Kobayashi S, Yoo W.-J, Yamashita Y. In Comprehensive Chirality, Vol. 4. Carreira EM, Yamamoto H. Elsevier; Amsterdam: 2012: 168-197
    • 46g Matsuo J.-I, Murakami M. Angew. Chem. Int. Ed. 2013; 52: 9109

      For background information about our chemistry on the silyl and acyl transfer agents, see the following accounts and reviews:
    • 47a Kita Y. Yakugaku Zasshi 1986; 106: 269
    • 47b Kita Y, Tamura O, Tamura Y. J. Synth. Org. Chem. Jpn. 1986; 44: 1118
    • 47c Tamura Y, Kita Y. J. Synth. Org. Chem. Jpn. 1988; 46: 205
    • 47d Kita Y, Shibata N. J. Synth. Org. Chem. Jpn. 1994; 52: 746
    • 47e Kita Y, Shibata N. Synlett 1996; 289
    • 47f Kita Y. Yakugaku Zasshi 1997; 117: 282
    • 47g Kita Y, Akai S. Chem. Rec. 2004; 4: 363
    • 48a Kita Y, Haruta J, Segawa J, Tamura Y. Tetrahedron Lett. 1979; 20: 4311
    • 48b Kita Y, Haruta J, Fujii T, Segawa J, Tamura Y. Synthesis 1981; 451
    • 48c Kita Y, Yasuda H, Sugiyama Y, Fukada F, Haruta J, Tamura Y. Tetrahedron Lett. 1983; 24: 1273
    • 49a Kita Y, Segawa J, Haruta J, Tamura Y. Tetrahedron Lett. 1980; 21: 3779
    • 49b Kita Y, Segawa J, Haruta J, Yasuda H, Tamura Y. J. Chem. Soc., Perkin Trans. 1 1982; 1099
    • 50a Kita Y, Yasuda H, Haruta J, Segawa J, Tamura Y. Synthesis 1982; 1089
    • 50b Kita Y, Yasuda H, Tamura O, Itoh F, Tamura Y. Tetrahedron Lett. 1984; 25: 4681
    • 50c Kita Y, Tamura O, Yasuda H, Itoh F, Tamura Y. Chem. Pharm. Bull. 1985; 33: 4235
    • 50d Kita Y, Tohma H, Inagaki M, Hatanaka K, Yakura T. J. Am. Chem. Soc. 1992; 114: 2175
    • 50e Kita Y, Shibata N, Kawano N, Tohjo T, Fujimori C, Ohishi H. J. Am. Chem. Soc. 1994; 116: 5116

    • For our recent report including the use of silyl transfer agent, see:
    • 50f Dohi T, Uchiyama T, Yamashita D, Washimi N, Kita Y. Tetrahedron Lett. 2011; 52: 2212
    • 51a Kita Y, Yasuda H, Tamura O, Itoh F, Ke YY, Tamura Y. Tetrahedron Lett. 1985; 26: 5777
    • 51b Kita Y, Tamura O, Itoh F, Yasuda H, Kishino H, Ke YY, Tamura Y. J. Org. Chem. 1988; 53: 554
    • 52a Kita Y, Ito F, Tamura O, Ke YY, Tamura Y. Tetrahedron Lett. 1987; 28: 1431
    • 52b Kita Y, Tamura O, Itoh F, Kishino H, Miki T, Kohno M, Tamura Y. J. Chem. Soc., Chem. Commun. 1988; 761
    • 52c Kita Y, Itoh F, Tamura O, Ke YY, Miki T, Tamura Y. Chem. Pharm. Bull. 1989; 37: 1446

      Selected recent examples:
    • 53a Matsushita K, Suzuki K, Ohmori K. Synlett 2017; 28: 944
    • 53b Finkbeiner P, Murai K, Röpke M, Sarpong R. J. Am. Chem. Soc. 2017; 139: 11349
    • 53c Sato S, Sakata K, Hashimoto Y, Takikawa H, Suzuki K. Angew. Chem. Int. Ed. 2017; 56: 12608
    • 53d Assal ME, Peixoto PA, Conffinier R, Garnier T, Deffieux D, Miqueu K, Sotiropoulos J.-M, Pouységu L, Quideau S. J. Org. Chem. 2017; 82: 11816
    • 53e Suzuki T, Watanabe S, Uyanik M, Ishihara K, Kobayashi S, Tanino K. Org. Lett. 2018; 20: 3919

      Dimerization of o-QMAs:
    • 54a Arjona O, Medel R, Plumet J. Tetrahedron Lett. 1999; 40: 8431
    • 54b Chittimalla SK, Liao C.-C. Tetrahedron 2003; 59: 4039
    • 54c McGrath NA, Bartlett ES, Sittihan S, Njardarson JT. Angew. Chem. Int. Ed. 2009; 48: 8543
    • 54d Chittimalla SK, Bandi C. RSC Adv. 2013; 3: 13663 ; see also ref. 53d
  • 55 Kita Y, Tohma H, Inagaki M, Hatanaka K. Heterocycles 1992; 33: 503
  • 56 Tohma H, Watanabe H, Takizawa S, Maegawa T, Kita Y. Heterocycles 1999; 51: 1785
  • 57 Ito M, Kubo H, Itani I, Morimoto K, Dohi T, Kita Y. J. Am. Chem. Soc. 2013; 135: 14078

    • For selected reviews, see:
    • 58a Crich D, Banerjee A. Acc. Chem. Res. 2007; 40: 151
    • 58b Ruiz-Sanchis P, Savina SA, Albericio F, Alvarez M. Chem. Eur. J. 2011; 17: 1388
    • 58c Ishikura M, Abe T, Choshi T, Hibino S. Nat. Prod. Rep. 2015; 32: 1389