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Nickel Catalysis Enables Hetero [2+2+1] Cycloaddition between Yne‐Isothiocyanates and Isonitriles with Low Catalyst Loading
Author(s) -
Liu RuiJuan,
Wang PengFei,
Yuan WenKui,
Wen LiRong,
Li Ming
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201601271
Subject(s) - chemistry , cycloaddition , nickel , catalysis , combinatorial chemistry , medicinal chemistry , organic chemistry
Abstract Nickel(II) can be used to catalyze the hetero [2+2+1] cycloaddition of 2‐alkynylaryl isothiocyanates and isonitriles in 2‐methyltetrahydrofuran (2‐MeTHF) to give a wide array of thieno[2,3‐ b ]indoles in excellent yields. The reaction is featured by employing as little as 0.3 mol% nickel(II) acetylacetonate [Ni(acac) 2 ] under air conditions in the absence of any additives (additional reducing agents and external ligands). This is the first successful example to apply nickel(II) directly in hetero [2+2+1] cycloadditions.