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On the Ring‐Opening of Some 3‐Lithiobithienyls and 3′‐Lithio‐α‐terthienyls
Author(s) -
Gronowitz Salo,
Svensson Arne
Publication year - 1986
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198600004
Subject(s) - phenyllithium , chemistry , halogen , ring (chemistry) , iodide , medicinal chemistry , catalysis , methyl iodide , stereochemistry , organic chemistry , alkyl
3‐Halobithienyls have been prepared through the Pd(PPh 3 ) 4 ‐catalyzed coupling of thiopheneboronic acids with 2,4‐dihalothiophenes. The ring‐opening of the corresponding 3‐lithiobithienyls obtained upon halogen‐metal exchange with phenyllithium has been investigated. Compound 12 , 3′‐iodo‐2,2′,2″‐terthienyl, was prepared in one step through the Pd(PPh 3 ) 4 ‐catalyzed coupling of two equivalents of 2‐thiopheneboronic acid with 2,3,5‐triiodothiophene. Treatment of 12 with phenyllithium and methyl iodide gave a mixture of compounds 10 and 11 occurring in Berkheya and Cullumia species.