Aromatic Metamorphosis of Dibenzothiophenes

Hideki Yorimitsu; Dhananjayan Vasu; M. Bhanuchandra; Kei Murakami; Atsuhiro Osuka

doi:10.1055/s-0035-1561617

Synlett, Table of Contents

Synlett 2016; 27(12): 1765-1774
DOI: 10.1055/s-0035-1561617

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Aromatic Metamorphosis of Dibenzothiophenes

Hideki Yorimitsu*

^aDepartment of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan

^bInstitute for Molecular Science, Okazaki, Aichi 444-8787, Japan

,

Dhananjayan Vasu

^aDepartment of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan

,

M. Bhanuchandra

^aDepartment of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan

,

Kei Murakami

^aDepartment of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan

^cThe Hakubi Center for Advanced Research, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan Email: yori@kuchem.kyoto-u.ac.jp

,

Atsuhiro Osuka

^aDepartment of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan

› Author Affiliations

Abstract

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Abstract

In general, aromatic cores are stable owing to their resonance energies. Different from facile peripheral modifications of aromatic cores, transforming an aromatic core into a different skeleton is ambitious and has attracted only little attention as a general synthetic method. This personal account shows our journey to inventing transformations of dibenzothiophenes into triphenylenes, carbazoles, and spirocyclic diarylfluorenes and to establishing ‘aromatic metamorphosis’ as a useful and game-changing strategy in organic synthesis.

1 Introduction

2 Aromatic Metamorphosis

3 From Dibenzothiophenes to Triphenylenes

4 From Dibenzothiophenes to Carbazoles

5 From Dibenzothiophenes to Spirocyclic Tetraarylmethanes

6 Conclusion

Key words

dibenzothiophenes - palladium - arylations - nucleophilic aromatic substitution - umpolung

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References

References
1 Current address: Department of Chemistry, Center for Catalytic Hydrocarbon Functionalizations Korea Advanced Institute of Science and Technology, Daejeon 34141, Republic of Korea.
2 Current address: Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan.
3 Current address: Department of Chemistry, School of Chemical Sciences and Pharmacy, Central University of Rajasthan, Bandarsindri, Rajasthan 305817, India.

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