The Synthesis of Conjugated Bis-Aryl Vinyl Substrates and Their Photoelectrocyclization Reactions towards Phenanthrene Derivatives

Abstract

The photoelectrocyclization of conjugated vinyl biaryls has proven to be a valuable and efficient strategy for generating phenanthrene derivatives. Contained in this review is an overview of the mechanism for the transformation and a discussion of the reaction scope with a focus on the electrocyclization itself, rearomatization, and the application of the reaction in natural product synthesis.

1 Introduction

2 The Synthesis of Conjugated Vinyl Biaryls

3 Mechanistic Studies

4 Substrate Scope

5 Applications

6 Conclusions

Key words

electrocyclization - photochemistry - cross-coupling - singlet-excited state - triplet-excited state - aromaticity - dihydrophenanthrene - natural product synthesis

Publication History

Received: 27 October 2020

Accepted after revision: 24 November 2020

Article published online:
11 January 2021

• References

• 1 New address: X. Zhao, Department of Chemistry, University of Pennsylvania, Philadelphia, PA, USA
• 2a Tóth B, Hohmann J, Vasas A. J. Nat. Prod. 2018; 81: 661
• 2b Kovacs A, Vasas A, Hohmann J. Phytochemistry 2008; 69: 1084
• 2c Li J, Hu G, Wang N, Hu T, Wen Q, Lu P, Wang Y. J. Org. Chem. 2013; 78: 3001
• 3 Mallory FB, Mallory CW. Org. React. 1984; 30: 1
• 4a Zhao X, Rainier JD. Tetrahedron 2017; 73: 4786
• 4b Zhao X, Song C, Rainier JD. Org. Lett. 2019; 21: 8611
• 4c Zhao X, Song C, Rainier JD. J. Org. Chem. 2020; 85: 5449
• 5 Horgan SW, Morgan DD, Orchin M. J. Org. Chem. 1973; 38: 3801
• 6 Padwa A, Doubleday C, Mazzu A. J. Org. Chem. 1977; 42: 3271
• 7 Kende AS, Curran DP. J. Am. Chem. Soc. 1978; 101: 1857
• 8 Markey MD, Fu Y, Kelly TR. Org. Lett. 2007; 9: 3255
• 9 Lewis FD, Zuo X, Gevorgyan V, Rubin M. J. Am. Chem. Soc. 2002; 124: 13664
• 10 Sloman DL, Mitasev B, Scully SS, Beutler JA, Porco JA. Jr. Angew. Chem. Int. Ed. 2011; 50: 2511
• 11a Sutton AE, Clardy J. Tetrahedron Lett. 2001; 42: 547
• 11b Wang C, Glorius F. Angew. Chem. Int. Ed. 2009; 48: 5240
• 12a Jana S, Rainier JD. Org. Lett. 2013; 15: 4426
• 12b Rallabandi R, Jana S, Rainier JD. Tetrahedron Lett. 2015; 56: 3538
• 13 Cheval NP, Dikova A, Blanc A, Weibel J.-M, Pale P. Chem. Eur. J. 2013; 19: 8765
• 14 Zhou Q, Zhang B, Su L, Jiang T, Chen R, Du T, Ye Y, Shen J, Dai G, Han D, Jiang H. Tetrahedron 2013; 69: 10996
• 15 Mao L, Sakurai H, Hirao T. Synthesis 2004; 2535
• 16a Vedejs E, Luchetta LM. J. Org. Chem. 1999; 64: 1011
• 16b Li B, Buzon RA, Zhang Z. Org. Process Res. Dev. 2007; 11: 951
• 17 Kan J, Huang S, Lin J, Zhang M, Su W. Angew. Chem. Int. Ed. 2015; 54: 2199
• 18 Souillart L, Cramer N. Chem. Eur. J. 2015; 21: 1863
• 19a Terao K, Toshimitsu A, Uemura S. J. Org. Chem. 1982; 47: 1837
• 19b Müller S, Liepold B, Roth GJ, Bestmann HJ. Synlett 1996; 521
• 20 Hayward RJ, Leznoff CC. Tetrahedron 1971; 27: 5115
• 21 Alabugin IV, Manoharan M, Breiner B, Lewis FD. J. Am. Chem. Soc. 2003; 125: 9329
• 22 Lapouyade R, Koussini R, Noumamode A, Courseille C. J. Chem. Soc., Chem. Commun. 1980; 740
• 23 Lazare S, Lapouyade R, Bonneau R. J. Am. Chem. Soc. 1985; 107: 6604
• 24 Lewis FD, Zuo X. Photochem. Photobiol. Sci. 2003; 2: 1059
• 25a Jacobs HJ. C, Havinga E. Adv. Photochem. 1979; 11: 305
• 25b Mazzucator U, Momicchioli F. Chem. Rev. 1991; 91: 1679
• 26 Op het Veld PH. G, Laarhoven WH. J. Chem. Soc., Perkin Trans. 2 1978; 915
• 27 Espejo VR, Rainier JD. Org. Lett. 2010; 12: 2154
• 28 A notable exception came from styryl pyridines, see: Lewis FD, Kalgutkar RS, Yang J.-S. J. Am. Chem. Soc. 2001; 123: 3878
• 29 Liu L, Yang B, Katz TJ, Poindexter MK. J. Org. Chem. 1991; 56: 3769
• 30 Winter DK, Endoma-Arias MA, Hudlicky T, Beutler JA, Porco JA. J. Org. Chem. 2013; 78: 7617