New method for C-H arylation/alkylation at α-position of cyclic aliphatic ethers by iron-oxide mediated reaction.
We report a new and efficient iron oxide catalyzed cross-coupling reaction between organometallic species such as alkyl/arylmagnesium halides or organolithium species and α-hydrogen bearing cyclic unbranched and branched aliphatic ethers via activation of C(sp(3))-H. In the presence of 1 mol% of iron oxide, five and six membered unbranched cyclic ethers such as tetrahydrofuran and tetrahydropyran gave good to excellent yields of cross-coupled products. Whereas, in case of branched ether such as 2-methyltetrahydrofuran, it was observed that the arylation occurred at both the sides and gave moderate yields of a mixture of regioisomers. Among the organometallic species used, alkyl organometallic reagents gave less yields as compared to aryl organometallics.
Medicinal Chemistry Division, Indian Institute of Integrative Medicine (Council of Scientific & Industrial Research), Jammu, 180 001, India. ppsingh@iiim.res.in
Parvinder Pal
PP
Singh
Satish
S
Gudup
Hariprasad
H
Aruri
Umed
U
Singh
Srinivas
S
Ambala
Mahipal
M
Yadav
Sanghapal D
SD
Sawant
Ram A
RA
Vishwakarma
D000478:Alkylation; D002384:Catalysis; D004988:Ethers, Cyclic / Q000737:chemistry*; D005290:Ferric Compounds / Q000737:chemistry*; D015394:Molecular Structure
D004988:Ethers, Cyclic; D005290:Ferric Compounds; C000499:ferric oxide