10354-50-4Relevant articles and documents
Amidation via ligand-free direct oxidative C(sp3)-H/N[sbnd]H coupling with Cu-CPO-27 metal-organic framework as a recyclable heterogeneous catalyst
Hoang, Thanh T.,Nguyen, Hanh T.H.,Le, Tien T.,Le, Dung T.,Truong, Thanh,Phan, Nam T.S.
, p. 8241 - 8251 (2016)
A copper-based metal-organic framework Cu-CPO-27 was synthesized, and used as a recyclable catalyst for the amidation of unactivated alkanes by benzamides via direct oxidative C(sp3)-H/N[sbnd]H coupling under ligand-free conditions. Using a catalytic amount of the Cu-CPO-27 for the transformation, high yields of N-cyclohexyl benzamides were achieved. The Cu-CPO-27 was more catalytically active than other Cu-MOFs such as Cu3(BTC)2, Cu(BDC), Cu(EDB), Cu2(BPDC)2(BPY), Cu2(BDC)2(DABCO), and Cu2(EDB)2(BPY). The Cu-CPO-27 also exhibited advantages as compared to several copper-based salts, including Cu(OAc)2, CuCl2, CuBr, CuI, CuCl, Cu(NO3)2, and CuSO4. The Cu-CPO-27 catalyst could be reused several times for the amidation transformation while its catalytic activity was not decreased significantly. To the best of our knowledge, the amidation of unactivated alkanes by benzamides via direct oxidative C(sp3)-H/N[sbnd]H coupling was not previously performed under heterogeneous catalysis conditions.
Reaction of N-fluoropyridinium fluoride with isonitriles and TMSN 3: A convenient one-pot synthesis of tetrazol-5-yl pyridines
Kiselyov, Alexander S.
, p. 4851 - 4854 (2005)
Reaction of N-fluoropyridinium fluoride generated in situ with a series of isonitriles and TMSN3 led to the formation of the corresponding tetrazol-5-yl pyridines in good yields (37-84%). A similar reaction sequence for quinoline yielded the respective derivatives of 2-quinoline. The proposed reaction mechanism involves the intermediate formation of a highly reactive carbene species.
Iridium(III)-Catalyzed Regioselective Intermolecular Unactivated Secondary Csp3?H Bond Amidation
Xiao, Xinsheng,Hou, Cheng,Zhang, Zhenhui,Ke, Zhuofeng,Lan, Jianyong,Jiang, Huanfeng,Zeng, Wei
, p. 11897 - 11901 (2016)
For the first time, a highly regioselective intermolecular sulfonylamidation unactivated secondary Csp3?H bond has been achieved using IrIIIcatalysts. The introduced N,N’-bichelating ligand plays a crucial role in enabling iridium–nitrene insertion into a secondary Csp3?H bond via an outer-sphere pathway. Mechanistic studies and density functional theory (DFT) calculations demonstrated that a two-electron concerted nitrene insertion was involved in this Csp3?H amidation process. This method tolerates a broad range of linear and branched-chain N-alkylamides, and provides efficient access to diverse γ-sulfonamido-substituted aliphatic amines.
Expedient Synthesis of Bridged Bicyclic Nitrogen Scaffolds via Orthogonal Tandem Catalysis
Bheemireddy, Narendraprasad Reddy,Biswas, Sovan,Evano, Gwilherm,Maes, Bert U. W.,Van Steijvoort, Ben F.,Waeterschoot, Marjo
supporting information, p. 21988 - 21996 (2021/08/13)
Bridged nitrogen bicyclic skeletons have been accessed via unprecedented site- and diastereoselective orthogonal tandem catalysis from readily accessible reactants in a step economic manner. Directed Pd-catalyzed γ-C(sp3)-H olefination of aminocyclohexane with gem-dibromoalkenes, followed by a consecutive intramolecular Cu-catalyzed amidation of the 1-bromo-1-alkenylated product delivers the interesting normorphan skeleton. The tandem protocol can be applied on substituted aminocyclohexanes and aminoheterocycles, easily providing access to the corresponding substituted, aza- and oxa-analogues. The Cu catalyst of the Ullmann-Goldberg reaction additionally avoids off-cycle Pd catalyst scavenging by alkenylated reaction product. The picolinamide directing group stabilizes the enamine of the 7-alkylidenenormorphan, allowing further product post functionalizations. Without Cu catalyst, regio- and diastereoselective Pd-catalyzed γ-C(sp3)-H olefination is achieved.
