Download PDF
Diver, S. T. et al.: 2022 Science of Synthesis, 2022/2: Knowledge Updates 2022/2 DOI: 10.1055/sos-SD-110-02138
Knowledge Updates 2022/2

10.17 Benzo[b]phospholes

More Information

Book

Editors: Diver, S. T.; Donohoe, T. J.; Joule, J. A.

Authors: Aitken, R. A. ; Behlow, K. T.; Chandra, D. ; Clark, J. R. ; Gupta, S. S. ; Kumar, R. ; Mills, M. D.; Sharma, U. ; Sloane, S. E.

Title: Knowledge Updates 2022/2

Print ISBN: 9783132451933; Online ISBN: 9783132451957; Book DOI: 10.1055/b000000642

1st edition © 2022. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Knowledge Updates



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fuerstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

Also available at
 


Abstract

This chapter is a complete revision and update of the earlier Science of Synthesis contribution from 2000 describing methods for the synthesis of benzo[b]phospholes. About half of the references cited describe newer methods reported between 2000 and 2021 and, as well as extensions to the previously described approaches, several completely new approaches are included. Among the strategies covered are reactions of metalated phenylalkyne derivatives with phosphorus halides, cyclizations of (2-alkynylphenyl)phosphorus compounds, direct reactions of phenylphosphorus compounds with alkynes, and aromatization of dihydro derivatives. In addition, the initially obtained compounds can be converted into a variety of derivatives by modification at phosphorus by oxidation, substitution, or reduction.

Key words

heterocycles - benzophospholes - phospholes - phosphorus compounds - ring closure - aromatization
 
  • 1 Quin LD, Comprehensive Heterocyclic Chemistry II. Katritzky AR, Rees CW, Scriven EFV. Elsevier; Oxford 1996. Vol. 2, p 757.
    Google Scholar
  • 2 Quin LD, Hughes AN, The Chemistry of Organophosphorus Compounds. Hartley FR. Wiley; Chichester 1990. Vol. 1, p 295.
    Google Scholar
  • 3 Rausch MD, Klemann LP. J. Am. Chem. Soc.. 1967; 89: 5732
    Google Scholar
  • 4 Egan W, Tang R, Zon G, Mislow K. J. Am. Chem. Soc.. 1971; 93: 6205
    Google Scholar
  • 5 Kurita J, Ishii M, Yasuike S, Tsuchiya T. J. Chem. Soc., Chem. Commun.. 1993; 1309
    Google Scholar
  • 6 Decken A, Bottomley F, Wilkins BE, Gill ED. Organometallics. 2004; 23: 3683
    Google Scholar
  • 7 Wu B, Santra M, Yoshikai N. Angew. Chem. Int. Ed.. 2014; 53: 7543
    Google Scholar
  • 8 Miquel Y, Igau A, Donnadieu B, Majoral J.-P, Dupuis L, Pirio N, Meunier P. Chem. Commun. (Cambridge). 1997; 279
    Google Scholar
  • 9 Parke SM, Tanaka S, Yu H, Hupf E, Ferguson MJ, Zhou Y, Naka K, Rivard E. Macromolecules. 2019; 52: 7477
    Google Scholar
  • 10 Fridland SV, Malkov YuK, Efremov AI. Zh. Obshch. Khim.. 1978; 48: 361 Chem. Abstr.. 1978; 88: 190 991m
    Google Scholar
  • 11 Chen Y.-R, Duan W.-L. J. Am. Chem. Soc.. 2013; 135: 16 754
    Google Scholar
  • 12 Unoh Y, Hirano K, Satoh T, Miura M. Angew. Chem. Int. Ed.. 2013; 52: 12 975
    Google Scholar
  • 13 Zhang P, Gao Y, Zhang L, Li Z, Liu Y, Tang G, Zhao Y. Adv. Synth. Catal.. 2016; 358: 138
    Google Scholar
  • 14 Ma D, Chen W, Hu G, Zhang Y, Gao Y, Yin Y, Zhao Y. Green Chem.. 2016; 18: 3522
    Google Scholar
  • 15 Quint V, Morlet-Savary F, Lohier J.-F, Lalevée J, Gaumont A.-C, Lakhdar S. J. Am. Chem. Soc.. 2016; 138: 7436
    Google Scholar
  • 16 Bu F, Wang E, Peng Q, Hu R, Qin A, Zhao Z, Tang BZ. Chem.–Eur. J.. 2015; 21: 4440
    Google Scholar
  • 17 Zhen S, Guo J, Luo W, Qin A, Zhao Z, Tang BZ. J. Photochem. Photobiol., A. 2018; 355: 274
    Google Scholar
  • 18 Hou H, Xu Y, Yang H, Yan C, Shi Y, Zhu S. Org. Biomol. Chem.. 2019; 17: 8175
    Google Scholar
  • 19 Hu G, Zhang Y, Su J, Li Z, Gao Y, Zhao Y. Org. Biomol. Chem.. 2015; 13: 8221
    Google Scholar
  • 20 Unoh Y, Yokoyama Y, Satoh T, Hirano K, Miura M. Org. Lett.. 2016; 18: 5436
    Google Scholar
  • 21 Ge Q, Zong J, Li B, Wang B. Org. Lett.. 2017; 19: 6670
    Google Scholar
  • 22 Märkl G, Jin GY, Berr K.-P. Tetrahedron Lett.. 1993; 34: 3103
    Google Scholar
  • 23 Tsuji H, Sato K, Ilies L, Itoh Y, Sato Y, Nakamura E. Org. Lett.. 2008; 10: 2263
    Google Scholar
  • 24 Sanji T, Shiraishi K, Kashiwabara T, Tanaka M. Org. Lett.. 2008; 10: 2689
    Google Scholar
  • 28 Fukazawa A, Ichihashi Y, Kosaka Y, Yamaguchi S. Chem.–Asian J.. 2009; 4: 1729
    Google Scholar
  • 29 Fukazawa A, Hara M, Okamoto T, Son E.-C, Xu C, Tamao K, Yamaguchi S. Org. Lett.. 2008; 10: 913
    Google Scholar
  • 30 Vedejs E, Steck PL. Angew. Chem. Int. Ed.. 1999; 38: 2788
    Google Scholar
  • 31 Xu Y, Wang Z, Gan Z, Xi Q, Duan Z, Mathey F. Org. Lett.. 2015; 17: 1732
    Google Scholar
  • 32 Zhou Y, Gan Z, Su B, Li J, Duan Z, Mathey F. Org. Lett.. 2015; 17: 5722
    Google Scholar
  • 33 Zhao X, Lu Z, Wang Q, Wei D, Lu Y, Duan Z, Mathey F. Organometallics. 2016; 35: 3440
    Google Scholar
  • 34 Cordaro JG, Stein D, Grützmacher H. J. Am. Chem. Soc.. 2006; 128: 14 962
    Google Scholar
  • 35 Zhang Y, Hu G, Ma D, Xu P, Gao Y, Zhao Y. Chem. Commun. (Cambridge). 2016; 52: 2815
    Google Scholar
  • 36 Liu L, Dong J, Yan Y, Yin S.-F, Han L.-B, Zhou Y. Chem. Commun. (Cambridge). 2019; 55: 233
    Google Scholar
  • 37 Santini CC, Fischer J, Mathey F, Mitschler A. J. Am. Chem. Soc.. 1980; 102: 5809
    Google Scholar
  • 38 Holah DG, Hughes AN, Kleemola D. J. Heterocycl. Chem.. 1977; 14: 705
    Google Scholar
  • 39 Mathey F. C. R. Seances Acad. Sci., Ser. C. 1969; 269: 1066
    Google Scholar
  • 40 Manz B, Kerth J, Maas G. Chem.–Eur. J.. 1998; 4: 903
    Google Scholar
  • 41 Collins DJ, Rowley LE, Swan JM. Aust. J. Chem.. 1974; 27: 831
    Google Scholar
  • 42 Nief F, Charrier C, Mathey F, Simalty M. Phosphorus, Sulfur Silicon Relat. Elem.. 1982; 13: 259
    Google Scholar
  • 44 Sedqui A, Lakhlifi T, Laude B, Amaudrut J. Bull. Soc. Chim. Belg.. 1989; 98: 865
    Google Scholar
  • 45 Quin LD, Mesch KA, Orton WL. Phosphorus, Sulfur Silicon Relat. Elem.. 1982; 12: 161
    Google Scholar
  • 46 Yoshifuji M, Shima I, Ando K, Imamoto N. Tetrahedron Lett.. 1983; 24: 933
    Google Scholar
  • 47 Aitken RA, Clasper PN, Wilson NJ. Tetrahedron Lett.. 1999; 40: 5271
    Google Scholar
  • 49 Hayashi M, Nishimura Y, Watanabe Y. Chem. Lett.. 2017; 46: 1732
    Google Scholar
  • 50 Hughes AN, Amornraksa K, Phisithkul S, Reutrakul V. J. Heterocycl. Chem.. 1976; 13: 65
    Google Scholar
  • 51 Koyanagi Y, Kawaguchi S, Fujii K, Kimura Y, Sasamori T, Tokitoh N, Matano Y. Dalton Trans.. 2017; 46: 9517
    Google Scholar
  • 52 Hayashi Y, Matano Y, Suda K, Kimura Y, Nakao Y, Imahori H. Chem.–Eur. J.. 2012; 18: 15 972
    Google Scholar