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Aromatic Metamorphosis of Thiophenes by Means of Desulfurative Dilithiation
Author(s) -
Kaga Atsushi,
Iida Hirokazu,
Tsuchiya Shun,
Saito Hayate,
Nakano Koji,
Yorimitsu Hideki
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202005223
Subject(s) - heteroatom , electrophile , lithium (medication) , sulfur , phenylene , benzene , metamorphosis , aromaticity , chemistry , carbon fibers , organic chemistry , molecule , materials science , ring (chemistry) , polymer , catalysis , medicine , botany , larva , composite number , composite material , biology , endocrinology
A new mode of aromatic metamorphosis has been developed, which allows thiophenes and their benzo‐fused derivatives to be converted to a variety of exotic heteroles. This transformation involves 1) the efficient generation of key 1,4‐dianions by means of desulfurative dilithiation with lithium powder and 2) the subsequent trapping of the dianions with heteroatom electrophiles in a one‐pot manner. Via the desulfurative dilithiation, the sulfur atoms of thiophenes are replaced also with a carbon–carbon double bond or a 1,2‐phenylene for the construction of benzene rings.