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Csp3–P versus Csp2–P Bond Formation: Catalyst-Controlled Highly Regioselective Tandem Reaction of Ene-Yne-Ketones with H-Phosphonates

Author:
Yu, Yue, Yi, Songjian, Zhu, Chuanle, Hu, Weigao, Gao, Bingjie, Chen, Yang, Wu, Wanqing, Jiang, Huanfeng
Source:
Organic letters 2016 v.18 no.3 pp. 400-403
ISSN:
1523-7052
Subject:
carbenes, catalysts, chemical reactions, chemical structure, copper, furans, nuclear magnetic resonance spectroscopy, oxidants, phosphorus, regioselectivity, stable isotopes
Abstract:
Under copper-catalyzed or base-promoted conditions, a wide range of ene-yne-ketones react with H-phosphonates to afford various phosphorylated furans in good yields. A copper carbene generation or a Michael addition is proposed as the key step in the selective construction of the Csp³–P or Csp²–P bond, which is supported by carbene capture reactions and interval ³¹P NMR experiments. Furthermore, this method features inexpensive metal catalysts, no usage of oxidant, and high atom economy, which make it attractive and practical.
Agid:
5792271