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....

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Veröffentlicht in:	Organic letters 2014-12, Vol.16 (23), p.6204-6207
Hauptverfasser:	Liu, Jianquan, Liu, Zhenhua, Liao, Peiqiu, Bi, Xihe
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkynes - chemistry Benzene Derivatives - chemical synthesis Benzene Derivatives - chemistry Catalysis Heterocyclic Compounds, 2-Ring - chemical synthesis Heterocyclic Compounds, 2-Ring - chemistry Molecular Structure Nitriles - chemistry Propanols - chemistry Silver - chemistry Sulfones - chemical synthesis Sulfones - chemistry
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Beschreibung
Zusammenfassung:	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.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol5031316