Stille coupling for the synthesis of isoflavones by a reusable palladium catalyst in water

被引：4

作者：

Chang, Ya-Ting ^{[1
]}

Liu, Ling-Jun ^{[1
]}

Peng, Wen-Sheng ^{[1
]}

Lin, Lin-Ting ^{[2
]}

Chan, Yi-Tsu ^{[2
]}

Tsai, Fu-Yu ^{[1
]}

机构：

[1] Natl Taipei Univ Technol, Inst Organ & Polymer Mat, 1,Sec 3,Chung Hsiao E Rd, Taipei 10608, Taiwan

[2] Natl Taiwan Univ, Dept Chem, Taipei, Taiwan

来源：

JOURNAL OF THE CHINESE CHEMICAL SOCIETY | 2021年 / 68卷 / 03期

关键词：

isoflavone; natural product; reusable catalyst; Stille coupling; water; ONE-POT SYNTHESIS; ARYLBORONIC ACIDS; SUZUKI-MIYAURA; STEREOSELECTIVE-SYNTHESIS; EFFICIENT; FLAVANONES; FACILE; ROUTE; 2'-HYDROXYCHALCONES; REARRANGEMENT;

D O I：

10.1002/jccs.202000478

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Isoflavones were synthesized from the reaction of 3-bromochromone derivatives and aryltributylstannanes via Stille coupling catalyzed by a water-soluble and reusable PdCl2(NH3)(2)/2,2 '-cationic bipyridyl system in aqueous solution. For prototype 3-bromochromone, the coupling reaction was performed at 80 degrees C for 24 hr with 2.5 mol% catalyst in water in the presence of tetrabutylammonium fluoride. After the reaction, the aqueous solution could be reused for several runs, indicating that its activity was only slightly decreased. For substituted 3-bromochromones, the addition of NaHCO3 and a higher reaction temperature (120 degrees C) were required to gain satisfactory outcomes. In addition, naturally occurring products, such as daidzein, could be obtained by this protocol via a one-pot reaction.

引用

页码：469 / 475

页数：7

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