Aromatic Metamorphosis of Dibenzothiophenes

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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• 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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