Modular synthesis of sulfonyl benzoheteroles by silver-catalyzed heteroaromatization of propargylic alcohols with p-toluenesulfonylmethyl isocyanide (TosMIC): dual roles of TosMIC.
A new silver-catalyzed heteroaromatization of propargylic alcohols with p-toluenesulfonylmethyl isocyanide (TosMIC) has been developed that provides an efficient and modular approach to sulfonyl benzoheteroles. For the first time, TosMIC plays a dual role in one reaction: sulfonyl source and ligand. An unprecedented deoxysulfonylation/hydration/condensation reaction pathway is disclosed.
†Department of Chemistry, Northeast Normal University, Changchun 130024, China.
Jianquan
J
Liu
†Department of Chemistry, Northeast Normal University, Changchun 130024, China.
Zhenhua
Z
Liu
†Department of Chemistry, Northeast Normal University, Changchun 130024, China.
Peiqiu
P
Liao
†Department of Chemistry, Northeast Normal University, Changchun 130024, China.|‡State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China.
Xihe
X
Bi
D000480:Alkynes / Q000737:chemistry*; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry*; D012834:Silver / Q000737:chemistry*; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry
D000480:Alkynes; D001555:Benzene Derivatives; D006574:Heterocyclic Compounds, 2-Ring; D009570:Nitriles; D020005:Propanols; D013450:Sulfones; D012834:Silver; C028255:propargyl alcohol