35027-76-0Relevant academic research and scientific papers
Photochemical Nickel-Catalyzed C-H Arylation: Synthetic Scope and Mechanistic Investigations
Heitz, Drew R.,Tellis, John C.,Molander, Gary A.
, p. 12715 - 12718 (2016)
An iridium photocatalyst and visible light facilitate a room temperature, nickel-catalyzed coupling of (hetero)aryl bromides with activated α-heterosubstituted or benzylic C(sp3)-H bonds. Mechanistic investigations on this unprecedented transformation have uncovered the possibility of an unexpected mechanism hypothesized to involve a Ni-Br homolysis event from an excited-state nickel complex. The resultant bromine radical is thought to abstract weak C(sp3)-H bonds to generate reactive alkyl radicals that can be engaged in Ni-catalyzed arylation. Evidence suggests that the iridium photocatalyst facilitates nickel excitation and bromine radical generation via triplet-triplet energy transfer.
New method for C-H arylation/alkylation at α-position of cyclic aliphatic ethers by iron-oxide mediated reaction
Singh, Parvinder Pal,Gudup, Satish,Aruri, Hariprasad,Singh, Umed,Ambala, Srinivas,Yadav, Mahipal,Sawant, Sanghapal D.,Vishwakarma, Ram A.
experimental part, p. 1587 - 1597 (2012/03/22)
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(sp3)-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.
Iron oxide mediated direct C-H arylation/alkylation at α-position of cyclic aliphatic ethers
Singh, Parvinder Pal,Gudup, Satish,Ambala, Srinivas,Singh, Umed,Dadhwal, Sumit,Singh, Baldev,Sawant, Sanghapal D.,Vishwakarma, Ram A.
supporting information; experimental part, p. 5852 - 5854 (2011/06/26)
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 aliphatic ethers via activation of C(sp3)-H. This is the first example of iron oxide mediated direct C-C bond formation without expensive or toxic ligands.
