COA of Formula: C8H12BCuF4N4. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: Copper(I) tetra(acetonitrile) tetrafluoroborate, is researched, Molecular C8H12BCuF4N4, CAS is 15418-29-8, about Enantioselective cyanation of remote C-H bonds via cooperative photoredox and copper catalysis. Author is Cheng, Zhongming; Chen, Pinhong; Liu, Guosheng.
Optically pure alkylnitriles are important structural motifs found in agrochems., pharmaceuticals, and natural products, which can be further transferred to acids, amines and amides. Direct asym. cyanation of sp3 C-H bonds represents the most efficient synthetic pathway to these optically pure alkylnitriles. However, selective functionalization of sp3 C-H bonds remains a crucial issue due to the inertness of sp3 C-H bonds as well as the difficulties in the control of stereo and regioselectivity. Inspired by enzymic oxygenases and halogenases, such as cytochrome P 450 and nonheme iron enzymes, the radical-based C-H functionalization has received much attention, which was initiated with a hydrogen atom transfer (HAT) process. Recently, numerous reports have been disclosed for the highly efficient functionalization of C-H bonds with an intramol. HAT process as a key step to govern the reactivity and site selectivity. Our group has developed a copper-catalyzed radical relay process for the enantioselective cyanation and arylation of benzylic C-H bonds using TMSCN and ArB(OH)2 as nucleophiles resp. Mechanistic studies indicated that a benzylic radical generated via a radical replay process can be trapped by a reactive chiral copper (II) cyanide enantioselectively, delivering optically pure benzyl nitriles efficiently. Herein, we communicate the catalytic asym. cyanation of remote C-H bonds by merging photoredox catalysis with copper catalysis. This reaction proceeds under mild reaction conditions and exhibits good functional group compatibility as well as wide substrates scope. Addnl., the nitrile group was further reduced to amide under hydrogen atm. This reaction provides an efficient pathway to synthesize chiral δ-cyano alcs. and 1, 6-amino alcs. The general procedure is as following: in a dried sealed tube, substrate 1 (0.2 mmol, 1.0 equivalent), Cu(CH3CN)4PF6 (0.01 mmol, 5 mol%), L (0.015 mmol, 7.5 mol%) and Ir(ppy)3 (0.002 mmol, 1 mol%) were dissolved in dichloromethane (4.0 mL) under N2 atmosphere, and stirred for 30 min. Then, TMSCN (50μL, 0.4 mmol, 2 equivalent) was added slowly under N2 atmosphere. The tube was sealed with a Teflon-lined cap, and the mixture was stirred under the irradiation of blue LED for 1∼7 d. The reaction mixture was diluted with dichloromethane, filtered through a short pad of celite. A solution of TBAF (3 equivalent) and HOAc (3 equivalent) was added to the filtration. The mixture was stirred for 5 min and then washed with water (3×10 mL) and dried over anhydrous Na2SO4. After filtration and concentration, the residue was purified by silica gel chromatog. (eluent: petroleum ether/ethyl acetate) to afford target product.
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