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Copper‐Catalyzed Dehydrative Cyclization of 1‐(2‐Hydroxyphenyl)propargyl Alcohols with P(O)H Compounds for the Synthesis of 2‐Phosphorylmethylbenzofurans
Author(s) -
Zhang Ming,
Yang Jianlin,
Xu Qing,
Dong Chao,
Han LiBiao,
Shen Ruwei
Publication year - 2018
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.201701368
Subject(s) - chemistry , propargyl , catalysis , acetonitrile , benzofuran , copper , hexafluorophosphate , medicinal chemistry , organic chemistry , combinatorial chemistry , ionic liquid
A tetrakis(acetonitrile)copper(I) hexafluorophosphate [Cu(MeCN)PF 6 ]‐catalyzed dehydrative reaction of 1‐(2‐hydroxyphenyl)propargyl alcohols with diarylphosphine oxides has been developed to provide an efficient synthesis of phosphorylated benzofurans in good to high yields. In the presence of a catalytic amount of an organic base, a variety of H‐phosphonates and H‐phosphinates can also be employed as good substrates to produce the corresponding products in moderate yields. The reaction has significant economical and ecological advantages since the formation of a new C( sp 3 )–P bond and the benzofuran framework could both be achieved using an inexpensive copper catalyst with water produced as the sole by‐product. Some synthetic transformations of the product have also been demonstrated.