DIETHYL ETHYNYLPHOSPHONATE: A VERSATILE SYNTHON FOR THE PREPARATION OF 1-ALKYNYL-AND 1, 3-BUTADIY NE-1, 4-DIYLPHOSPHONATES

SG Dutremez, C Guerin, BJL Henner…

Index: Dutremez, Sylvain G.; Guerin, Christian; Henner, Bernard J.L.; Tomberli, Veronique Phosphorus, Sulfur and Silicon and Related Elements, 2000 , vol. 160, p. 251 - 269

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Citation Number: 11

Abstract

Abstract The cross-coupling reaction between diethyl ethynylphosphonate (1) and several aromatic iodides under the Sonogashira conditions (Cl2Pd (PPh3) 2/CuI/Et3N) gives only minute amounts of the expected 1-alkynylphosphonates. Yields of about 20% are achieved upon using Pd (OAc) 2/2PPh3/Et3N in place of the previous catalytic system. Side-reactions involving 1 and the mine are shown to be responsible for these low yields. Metalation of 1 ...

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