Difluorination of Functionalized Aromatic Olefins Using Hypervalent Iodine/HF Reagents
Difluorination of Functionalized Aromatic Olefins Using Hypervalent Iodine/HF Reagents
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DOI：
10.1021/acs.joc.8b02473
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发表时间：
2018-12-21
影响因子：
3.6
通讯作者：
Oyamada, Juzo
中科院分区：
文献类型：
--
作者：
Kitamura, Tsugio;Yoshida, Kento;Oyamada, Juzo
由PHIO和HF.py组成的高价碘/氢氟试剂对含有合成重要的羰基和羟基的官能化芳香烃的氟化反应是有效的。1，3-二苯基-2-丙烯-1-酮在CH2Cl2中与PHIO/HF.py试剂在室温下进行氟化反应，高产率地合成了3，3-二氟-1，2-二苯基-1-丙酮。其他α-芳基-α，β-不饱和酮经过氟化得到芳基2，2-二氟乙酮衍生物，产率从好到高。用p-Toli/HF.py/mCPBA试剂体系催化α-芳基-α，β-不饱和酮的氟化反应也很有效。此外，用PHIO/HF.py试剂对肉桂醇衍生物进行氟化反应，以适中的产率合成了2-芳基-3，3-二氟-1-丙醇。
The hypervalent iodine/HF reagent consisting of PhIO and HF.py was found to be effective for fluorination of functionalized aromatic olefins bearing synthetically important carbonyl and hydroxyl groups. Fluorination of 1,3-diphenyl-2-propen-1-one with PhIO/HF.py reagent in CH2Cl2 at room temperature gave 3,3-difluoro-1,2-diphenyl-1-propanone in high yield. Other alpha-aryl-alpha,beta-unsaturated ketones underwent the fluorination to yield aryl 2,2-difluoroethyl ketone derivatives in good to high yields. Catalytic fluorination of alpha-aryl-alpha,beta-unsaturated ketones using a p-TolI/HF.py/mCPBA reagent system also worked well. Moreover, the fluorination of cinnamyl alcohol derivatives by PhIO/HF.py reagent proceeded smoothly to afford 2-aryl-3,3-difluoro-1-propanols in moderate yields.