A straightforward synthesis of 1-azido-2-bromo-1,1,2,2-tetrafluoroethane on a multigram scale from 1,2-dibromotetrafluoroethane and sodium azide in a novel process initiated by organomagnesium compounds (i-PrMgCl·LiCl, turbo Grignard) is reported. Synthetic utility of the title azide in the preparation of N-tetrafluoroethylated and N-difluoromethylated five-membered nitrogen heterocycles was demonstrated with azide-alkyne cycloaddition to N-bromotetrafluoroethyl 1,2,3-triazoles, subsequent reduction to N-tetrafluoroethyl triazoles, rhodium-catalyzed transannulation with nitriles to N-tetrafluoroethylated imidazoles and rhodium-catalyzed ring-opening, and cyclization to N-difluoromethylated oxazoles and thiazoles.

中文翻译：

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1-叠氮基-2-溴-1,1,2,2-四氟乙烷的制备及其在合成N-氟烷基化氮杂环中的应用。

由1,2-二溴四氟乙烷和叠氮化钠在有机镁化合物（i- PrMgCl·LiCl，涡轮增压）引发的新方法中以克数形式直接合成1-azido-2-bromo-1,1,2,2-四氟乙烷格利雅（Grignard）。叠氮化物-炔环加成到N-溴四氟乙基1,2,3-三唑上，随后还原为N-四氟乙基三唑，铑证明了叠氮化物在N-四氟乙基化和N-二氟甲基化的五元氮杂环的制备中的合成效用用腈催化的环转移成N-四氟乙基化的咪唑和铑催化的开环，然后环化成N-二氟甲基化的恶唑和噻唑。