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

共 72 条

[1] Antiviral isoflavonoid sulfate and steroidal glycosides from the fruits of Solanum torvum [J].

Arthan, D ;

Svasti, J ;

Kittakoop, P ;

Pittayakhachonwut, D ;

Tanticharoen, M ;

Thebtaranonth, Y .

PHYTOCHEMISTRY, 2002, 59 (04) :459-463

[2] Recent advances in transition metal-catalysed cross-coupling of (hetero)aryl halides and analogues under ligand-free conditions [J].

Ayogu, Jude I. ;

Onoabedje, Efeturi A. .

CATALYSIS SCIENCE & TECHNOLOGY, 2019, 9 (19) :5233-5255

[3] An efficient "one pot" synthesis of isoflavones [J].

Balasubramanian, S ;

Nair, MG .

SYNTHETIC COMMUNICATIONS, 2000, 30 (03) :469-484

[4] The first isolation and crystal structure of a boron difluoro complex (isoflavone yellow). Biologically active intermediates produced during isoflavone synthesis [J].

Balasubramanian, S ;

Ward, DL ;

Nair, MG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (04) :567-569

[5] Development of a general approach to the synthesis of a library of isoflavonoid derivatives [J].

Biegasiewicz, Kyle F. ;

Gordon, James S. ;

Rodriguez, Deana A. ;

Priefer, Ronny .

TETRAHEDRON LETTERS, 2014, 55 (37) :5210-5212

[6] An efficient synthesis of daidzein, dimethyldaidzein, and isoformononetin [J].

Biegasiewicz, Kyle F. ;

St Denis, Jeffrey D. ;

Carroll, Vincent M. ;

Priefer, Ronny .

TETRAHEDRON LETTERS, 2010, 51 (33) :4408-4410

[7] Antiproliferative activity of various flavonoids and related compounds:: additive effect of interferon-α2b [J].

Blank, VC ;

Poll, C ;

Marder, M ;

Roguin, LP .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (01) :133-136

[8] INTRAMOLECULAR [2 + 2] KETENE CYCLO-ADDITIONS - SYNTHESIS OF ISOFLAVONES AND 3-AROYLBENZOFURANS [J].

BRADY, WT ;

GU, YQ .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (07) :1353-1356

[9]

Chan Y-T., 2021, J CHIN CHEM SOC-TAIP, P1

[10] Hiyama reaction of aryl bromides with arylsiloxanes catalyzed by a reusable palladium(II)/cationic bipyridyl system in water [J].

Chen, Shao-Nung ;

Wu, Wei-Yi ;

Tsai, Fu-Yu .

TETRAHEDRON, 2008, 64 (35) :8164-8168

← 1 2 3 4 5 6 7 8 →