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Synthesis of Benzofurans via Tandem Rhodium‐Catalyzed C( sp 3 )H Insertion and Copper‐Catalyzed Dehydrogenation
Author(s) -
Li Lin,
Xia XiaoHan,
Wang Yong,
Bora Pranjal P.,
Kang Qiang
Publication year - 2015
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.201500396
Subject(s) - chemistry , benzofuran , dehydrogenation , catalysis , rhodium , cascade reaction , alkyne , combinatorial chemistry , cycloaddition , tandem , cascade , yield (engineering) , copper , medicinal chemistry , organic chemistry , materials science , metallurgy , composite material , chromatography
Abstract A sequentially catalyzed cascade approach for the synthesis of benzofuran derivatives (up to 88% yield) from 1‐sulfonyl‐1,2,3‐triazoles has been developed. The cascade reaction involves sequential rhodium‐catalyzed C( sp 3 )H insertion and copper‐catalyzed aerobic oxidation. The method was made more convenient towards the synthesis of benzofurans starting from terminal alkynes via a one‐pot sequential copper‐catalyzed alkyne‐azide cycloaddition (CuAAC)/CH insertion/dehydrogenation cascade reaction. Moreover, the utility of the cascade approach was demonstrated in the synthesis of the indole framework.