CCS Chemistry ( IF 9.4 ) Pub Date : 2021-01-19 , DOI: 10.31635/ccschem.020.202000542 Jie Fang 1, 2 , Qiang Hu 1 , Wan-Li Dong 1 , Guo-Qiang Xu 1 , Xiu-Qin Hu 1 , Yong-Chun Luo 1 , Peng-Fei Xu 1
Direct introduction of a carboxyl group into molecules is one of the most useful methods for the preparation of carboxylic acids, which avoids the conversion of various preexisting functional groups and features good step- and atom-economy. However, the methods for the direct synthesis of two-carbon added carboxylic acids from the precursors remain rare. Herein, we first report a general and mild method for the direct synthesis of a range of aliphatic acids by photoredox-catalyzed hydrocarboxymethylation of alkenes with good toleration of various functional groups in which bromoacetic acid is utilized as an ideal two-carbon synthon. The synthetic utility of this hydrocarboxymethylation protocol is further demonstrated by the concise synthesis of two marketed drugs, sensipar and tirofiban, from commercially available starting materials.
中文翻译:
光氧化还原催化烯烃的羟羧甲基化
将羧基直接引入分子中是制备羧酸最有用的方法之一,它避免了各种预先存在的官能团的转化,并具有良好的步长和原子经济性。然而,从前体直接合成加有两个碳的羧酸的方法仍然很少。在本文中,我们首先报道了通过光催化还原烯烃的加氢羧甲基化并具有对各种官能团的良好耐受性的,直接合成一系列脂肪酸的一般温和方法,其中溴乙酸被用作理想的二碳合成子。该氢羧甲基化方案的合成效用进一步由市售起始原料合成两种市售药物sensipar和tirofiban进一步证明。