化学经纬
化学经纬

插羰反应制备羧酸衍生物

chem有机方法1061500

芳基和烯基卤化物在温和条件下的钯催化插羰反应是合成羧酸及其衍生物的非常有用的合成方法。反应机理是芳基和烯基卤化物先和Pd(0)发生氧化加成反应生成芳基或烯基钯配合物,然后CO插入到钯--碳键之间,还原消除,最后在醇或水等试剂的亲和进攻下就形成了相应的酯或羧酸。芳香的或α,β—不饱和的羧酸或酯就是芳基或烯基卤化物在水或醇中通过插羰反应制得的。

插羰反应制备羧酸衍生物 第1张

A solution ofN-(4-chlorobenzyl)-4-hydroxy-6-iodo-3-quinolinecarboxamide (30.0 g), Et3N(19.1 mL), MeOH (110.6 mL), Pd(OAc)2 (431 mg), and1,3-bis(diphenylphosphino)propane (791.9 mg) in 375 mL anhydrous DMF is stirredat room temperature until everything dissolves. The mixture is purgedby carbon monoxide at room temperature for 10 minutes, then is heated at 90 oCand stirred overnight under 40 psi of carbon monoxide.Thereaction is cooled to room temperature. The product is precipitated by adding160 mL 1 N HCl into the reaction mixture. An orange solid precipitates iscollected. The solid is triturated with EtOAc, filtered, and washed with CH2Cl2to afford 23.8 g (93 % yield) of the title compound as an off-white solid.

插羰反应制备羧酸衍生物 第2张

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