Synthesis of difluoromethyl ethers with difluoromethyltriflate.

Synthesis of difluoromethyl ethers with difluoromethyltriflate.
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DOI:
10.1002/anie.201209250
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发表时间:
2013-02-11
影响因子:
16.6
通讯作者:
Hartwig, John F.
Hartwig, John F.
中科院分区:
化学1区
文献类型:
--
作者:
Fier, Patrick S.;Hartwig, John F.

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Difluoromethyl ethers are found increasingly in pharmaceuticals, agrochemicals, and materials.[1] Aryl difluoromethyl ethers are found in medicinally important compounds that include enzyme inhibitors,[2] anti-HIV agents [3] and atimicrobial agents.[4] Pantoprazole (Protonix®), a proton-pump inhibitor, is among the top 100 pharmaceuticals and contains a difluoromethyl ether.[5]However, current syntheses of difluoromethyl ethers require the ozone-depleting compound HCF2Cl (Freon 22) that is difficult to handle because it is a gas (Scheme 1).[6] Non-ozonedepleting sources have been reported for the formation of difluoromethyl ethers from phenols,[7] but the reactions with these reagents often require high-temperatures, long reaction times, and have only been demonstrated to work with simple substrates.
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