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Iron‐Catalyzed Primary C—H Amination of Sulfamate Esters and Its Application in Synthesis of Azetidines †
Author(s) -
Zhang Yan,
Zhong Dayou,
Usman Muhammad,
Xue Peng,
Liu WenBo
Publication year - 2020
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.202000299
Subject(s) - chemistry , amination , nitrene , catalysis , intramolecular force , trifluoromethanesulfonate , primary (astronomy) , surface modification , organic chemistry , combinatorial chemistry , inert , physics , astronomy
Summary of main observation and conclusion The direct amination of unactivated primary C—H bonds is extremely challenging due to their inert nature. Herein, we report an intramolecular primary C—H amination of sulfamate esters using an iron catalyst derived from iron(II) triflate and bipyridine. An array of oxathiazinanes were synthesized in moderate to good yields, which were further converted into biologically important azetidines by a one‐pot procedure. This research demonstrates the potential of applying simple nitrogen ligands in iron‐catalyzed C—H functionalization and offers an accessible alternative to state‐of‐the‐art iron‐nitrene chemistry.