ChemicalBook CAS DataBase List BENZO(B)NAPHTHO(1,2-D)THIOPHENE

BENZO(B)NAPHTHO(1,2-D)THIOPHENE synthesis

6synthesis methods

Product Name:BENZO(B)NAPHTHO(1,2-D)THIOPHENE
CAS Number:205-43-6
Molecular formula:C16H10S
Molecular Weight:234.32

1599466-87-1
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$35.00/100mg

205-43-6
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$18.00/100mg

Yield:205-43-6 53%

Reaction Conditions:

with tris-(dibenzylideneacetone)dipalladium⁽⁰⁾;copper diacetate;sodium pivalate in N,N-dimethyl-formamide at 150; for 5 h;Inert atmosphere;

Steps:

General procedure for the preparation of dibenzothiophenes form the 2-iodinated diphenylthioethers using Pd₃(dba)₂:

General procedure: Under argon flush, a flask was charged with the substrates of diaryl thioethers (0.58 mmol), DMF (10 mL), Pd₃(dba)_{2 (105 mg, 0.115 mmol), Cu(OAc)2 (23 mg, 0.115 mmol) amd sodium pivalate hydrate (72 mg, 0.58 mmol), and then the mixture was maintained at 150°C with stirring for 5 h under argon atmosphere. After completion by TLC analysis, the reaction mixture was diluted with EtOAc and water. The aqueous phase was extracted with EtOAc twice and the combined organic phases were washed wtih brine and dried over MgSO4. Then solvent was evaporated under vacuum and the crude product was purified by column chromatography on silica gel. eluting with a mixture of petroleum ether and EtPAc to give dibenzothiophenes. Yields are listed in Table 2.}

References:

Chen, Ya-Fang;Ma, Rui-Yue;Zhou, Lu-Nan;Du, Zhenting;Zhang, Tao [Heterocycles,2016,vol. 92,# 10,p. 1874 - 1881]