Aromatic Metamorphosis of Thiophenes by Means of Desulfurative Dilithiation
Aromatic Metamorphosis of Thiophenes by Means of Desulfurative Dilithiation
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DOI：
10.1002/chem.202005223
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发表时间：
2021-02-05
影响因子：
4.3
通讯作者：
Yorimitsu, Hideki
中科院分区：
文献类型：
--
作者：
Kaga, Atsushi;Iida, Hirokazu;Yorimitsu, Hideki
一种新的芳族变态模式已经被开发出来，它允许噻吩及其苯并稠合衍生物被转化为各种奇异的杂环化合物。该转化涉及1）通过用锂粉脱硫的二硫代硫酸化有效生成关键的1，4-二价阴离子，和2）随后以一锅法用杂原子亲电试剂捕获二价阴离子。通过脱硫的二硫代噻吩化，噻吩的硫原子也被碳-碳双键或1，2-亚苯基取代以构建苯环。
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.