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

Tohru Kamitanaka; Koji Morimoto; Toshifumi Dohi; Yasuyuki Kita

doi:10.1055/s-0037-1611735

Synlett, Table of Contents

Synlett 2019; 30(10): 1125-1143
DOI: 10.1055/s-0037-1611735

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

Tohru Kamitanaka

^aResearch Organization of Science and Technology, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan Email: kita@ph.ritsumei.ac.jp

,

Koji Morimoto

^aResearch Organization of Science and Technology, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan Email: kita@ph.ritsumei.ac.jp

^bCollege of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan

,

Toshifumi Dohi

^aResearch Organization of Science and Technology, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan Email: kita@ph.ritsumei.ac.jp

^bCollege of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan

,

Yasuyuki Kita *

^aResearch Organization of Science and Technology, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan Email: kita@ph.ritsumei.ac.jp

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Abstract

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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

Key words

quinone monoacetal - coupling - biaryl synthesis - terphenyl - phenol - dihydrobenzofuran - α-aryl carbonyl

Full Text

References

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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