Facile synthesis of 4-acetyl-coumarins, -thiocoumarin and -quinolin-2(1H)-one via very high alpha-regioselective Heck coupling on tosylates

作者：Valente Sergio; Kirsch Gilbert^*

来源：Tetrahedron Letters, 2011, 52(27): 3429-3432.

DOI：10.1016/j.tetlet.2011.04.033

• 2H-1-Benzopyran-2-one
• Quinolin-2(1H)-one
• Heck coupling
• alpha-Regioselectivity

An efficient synthesis of a series of methyl ketones at the C4 position of coumarins, coumarin-containing heterocycles and analogous scaffolds is reported via very high alpha-regioselective Heck coupling using tosylates and in very high yields. Although o alpha-regioselectivity in Heck coupling can be obtained with triflates as substrates, tosylates are less toxic, less expensive and, importantly, more stable.

• 出版日期2011-7-6