An Atom‐Economic Approach for Vinylation of Indoles and Phenols Using Calcium Carbide as Acetylene Surrogate. Issue 25 (9th August 2016)

• Record Type: Journal Article
• Authors: Rattanangkool, Eakkaphon; Vilaivan, Tirayut; Sukwattanasinitt, Mongkol; Wacharasindhu, Sumrit
• Is Part Of: European journal of organic chemistry. Issue 25(2016)
• Page Start: 4347
• Page End: 4353
• Publication Date: 2016-08-09
• Subjects: Synthetic methods -- Nucleophilic addition -- Green chemistry -- Vinylation -- Nitrogen heterocycles -- Calcium carbide -- Acetylene gas; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600666
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : An efficient N ‐vinylation procedure for indoles and O ‐vinylation of phenols enabling facile access to N ‐vinyl indoles and phenyl vinyl ethers is reported. Vinylated products are generated in satisfactory to excellent yields (65–92 %) upon substrate treatment with calcium carbide in wet solvents under standard laboratory conditions