CAS: 147541-01-3; N-Fluoro-4,6-Dimethylpyridinium-2-Sulfonate

相似化合物

62516-08-9 89954-97-2 147540-88-3

📜4,6-Dimethylpyridine-2-Sulfonic Acid Triethylamine置于fluorine体系中,用 水,乙腈 用作溶剂,以78%的收率获得n-氟-4,6-二甲基吡啶-2-磺酸盐
参考文献:Highly Selective Fluorinating Agents: A Counteranion-Bound N-Fluoropyridinium Salt System
标题:Highly Selective Fluorinating Agents: A Counteranion-Bound N-Fluoropyridinium Salt System
摘要:A Series Of Alkyl-Or (Trifluoromethyl)-Substituted N-Fluoropyridinium-2-Sulfonates 2A-H,Differing In Fluorinating Power,Were Synthesized,And Assessment Was Made Of The Effectiveness Of Each Selective Fluorinating Agent. N-Fluoropyridinium-3-And-4-Sulfonates 3 And 4 Were Also Synthesized. Power-Variables 2A-H Were Found To Be Highly Selective Fluorinating Agents For A Wide Range Of Nucleophilic Substrates Such As Activated Aromatics,Enol Trialkylsilyl And Alkyl Ethers,Active Methylene Compounds,Activated Olefins,And Sulfides. Thus,Phenol,Naphthol,Phenylurethane,And The Trimethylsilyl Ether Of Phenol Were Exclusively Or Highly Selectively Fluorinated At The O-Position With 2F-H. Conjugated Enol Trialkylsilyl Ethers Of A Steroid Were Regioselectively Fluorinated At The 6-Position With Moderately Powerful 2B-E. This Regioselectivity Increased With The Bulkiness Of The Silyl Part,And With The Most Bulky Triisopropylsilyl Group Exclusive B-Fluorination Was Achieved. Preferential Beta-Stereoselective Fluorination At The 6-Position Was Observed. N-Fluoropyridinium-2-Sulfonates Were Activated With An Acid. This Acid-Catalyzed Fluorination Led To The Preferential P-Fluorination Of Anisole. The Present Results Can Be Explained Based On The Capacity Of The 2-Sulfonate Anion To Interact With The Hydroxy Group Of Phenol Or Naphthol,Nh Group Of Phenylurethane,Silicon Atoms Of Silyl Ethers,Or Protons Of Acids.
Doi:10.1021/jo00125A049

专利信息

专利号:US-8558012-B2
优先权日:2009-03-02
标 题:2-fluoro-1,3-benzodithiol 1,1,3,3-tetraoxide derivative, production method thereof, and production method of monofluoromethyl group-containing compound using the same
发明人：SHIBATA NORIO
权利人:SHIBATA NORIO; NAGOYA INST TECHNOLOGY; TOSOH P TECH INC
摘要:A 2-fluoro-1,3-benzodithiol 1,1,3,3-tetraoxide derivative as a monofluoromethyl group introduction agent that is effective as an intermediate in pharmaceutical and agrochemical synthesis, a production method thereof, and a production method of a monofluoromethyl group-containing compound using this 2-fluoro-1,3-benzodithiol 1,1,3,3-tetraoxide derivative are provided. The 2-fluoro-1,3-benzodithiol 1,1,3,3-tetraoxide derivative represented by the following general formula (1) (wherein R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom, a straight-chain or branched alkyl group having 1 to 4 carbon atoms, a straight-chain or branched alkyloxy group having 1 to 4 carbon atoms, a halogen atom, a nitro group, or a cyano group), the production method thereof, and various monofluoromethyl group-containing compounds are manufactured using this 2-fluoro-1,3-benzodithiol 1,1,3,3-tetraoxide derivative as a monofluoromethylating agent.