芳基重氮鹽可以發(fā)生的反應(yīng)最常見的就是Sandmeyer反應(yīng)可以制備鹵代芳烴,芳基酚或芳基腈,另外就是Balz-Schiemann反應(yīng)制備芳基氟化物,偶氮偶合反應(yīng)制備偶氮二芳基類化合物。1995年Beller等人報(bào)道了利用重氮鹽作為底物進(jìn)行Heck反應(yīng)制備芳基烯基化物,這是一種很實(shí)用的制備芳基烯烴的反應(yīng),此類反應(yīng)不需要膦催化劑和胺,條件溫和。
反應(yīng)實(shí)例(Beller,M.; Kuehlein, K. Synlett. 1995, 441)
a The Palladium is 5% of weight on the correspondingcatalyst support. b 2-EH = 2-ethylhexan-1-ol. c Already used catalyst.
Generalprocedure for the synthesis of cinnamic acid esters:
30 mmol of corresponding diazonium salt and 60 mmol of acrylic acid esterare suspended in 40 mL of the solvent. Subsequently, 0.6 mmol of palladium on activatedcharcoal (5% weight) is added at 0°C.Then the reaction mixture is heated to 60°C in the course of 1 hour and stirred for 12 hoursat this temperature. After cooling to room temperature, the catalyst isfiltered off and washed with the solvent. The solvent is evaporated in vacuoand the crude product is further purified by crystallized or chromatography onsilca.