Sequential and One-Pot Reactions of Phenols with Bromoalkynes for the Synthesis of (Z)-2-Bromovinyl Phenyl Ethers and Benzo[b]furans

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• 作者：Shihua Wang ; Pinhua Li ; Lin Yu ; Lei Wang
• 刊名：Organic Letters
• 出版年：2011
• 出版时间：November 18, 2011
• 年：2011
• 卷：13
• 期：22
• 页码：5968-5971
• 全文大小：738K
• 年卷期：v.13,no.22(November 18, 2011)
• ISSN：1523-7052

文摘

Benzo[b]furans were prepared in one pot based on the addition/palladium-catalyzed C鈥揌 bond functionalization of phenols with bromoalkynes. The addition reactions of phenols to bromoalkynes generated (Z)-2-bromovinyl phenyl ethers in high yields with excellent regio- and stereoselectivity. The obtained (Z)-2-bromovinyl phenyl ethers subsequently proceeded by intramolecular cyclization to afford 2-substituted benzo[b]furans in good yields through palladium-catalyzed direct C鈥揌 bond functionalizations. It is important to note that the transformation of phenols with bromoalkynes into benzo[b]furans could be carried out in one pot with a simple and efficient tandem procedure.