Premium
An Atom‐Economic Approach for Vinylation of Indoles and Phenols Using Calcium Carbide as Acetylene Surrogate
Author(s) -
Rattanangkool Eakkaphon,
Vilaivan Tirayut,
Sukwattanasinitt Mongkol,
Wacharasindhu Sumrit
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600666
Subject(s) - calcium carbide , chemistry , acetylene , phenols , catalysis , carbide , organic chemistry , calcium , metal , combinatorial chemistry
An efficient N ‐vinylation of indoles and O ‐vinylation of phenols to give N ‐vinyl indoles and phenyl vinyl ethers is reported. The vinylated products can be produced in satisfactory to excellent yields (65–92 %) upon treatment of indoles or phenols with calcium carbide in wet solvents in a standard laboratory setup. Key features of this reaction include the use of calcium carbide as a safe and inexpensive slow released acetylene source for N ‐ and O ‐vinylation under simple reaction conditions without the need for metal catalyst or halogenated substrates.