Synthesis of Dihydropyrrole Derivatives by a Palladium-Catalyzed Heck and Suzuki Cross-Coupling Cascade Reaction

被引：17

作者：

Peng, Jinsong ^{[1
,2
]}

Zhao, Yan ^{[1
]}

Zhou, Jingjie ^{[1
]}

Ding, Yuehang ^{[1
]}

Chen, Chunxia ^{[1
]}

机构：

[1] Northeast Forestry Univ, Dept Chem & Chem Engn, Coll Sci, Harbin 150040, Peoples R China

[2] Northeast Forestry Univ, Postdoctoral Mobile Res Stn Forestry Engn, Harbin 150040, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2014年 / 46卷 / 15期

基金：

中国博士后科学基金; 中国国家自然科学基金;

关键词：

pyrroles; palladium; catalysis; tandem reactions; Heck reaction; Suzuki reaction; ENANTIOSELECTIVE SYNTHESIS; NUCLEOPHILIC-ADDITION; STEREOSELECTIVE-SYNTHESIS; CYCLIZATION REACTION; FACILE PREPARATION; DOMINO REACTIONS; ORGANIC HALIDES; 2,3-DIHYDROPYRROLES; AZIRIDINES; BROMOALKYNES;

D O I：

10.1055/s-0033-1341265

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An expedient protocol for the synthesis of 5-aryl-2,3-dihydropyrroles, starting from N-tosyl-protected 2-methylprop-2-en-1-amine, alkynyl bromides, and arylboronic acids, is described. The sequential reaction sequence involves nucleophilic addition of the sulfonamide to the alkynyl bromide, followed by a palladium-catalyzed tandem intramolecular Heck and intermolecular Suzuki cross-coupling reaction of the bromoalkene adduct.

引用

页码：2051 / 2056

页数：6

共 50 条

[1] Stereocontrolled synthesis of (E)-stilbene derivatives by palladium-catalyzed Suzuki-Miyaura cross-coupling reaction
Rau, Hailee H.
Werner, Nathan S.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2018, 28 (16) : 2693 - 2696
[2] Stereocontrolled synthesis of (E)-stilbene derivatives by palladium-catalyzed Suzuki-Miyaura cross-coupling reaction
Rau, Hailee
Werner, Nathan
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
[3] Enantioselective Palladium-Catalyzed Cascade Narasaka-Heck Cyclization/Suzuki Coupling Reaction
Ye, Wenshao
Cao, Kangning
Ye, Zihao
Qi, Shutao
Yang, Junfeng
Zhang, Junliang
ACS CATALYSIS, 2025, 15 (03): : 2516 - 2521
[4] Efficient palladium-catalyzed Suzuki cross-coupling reaction with β-ketoamine ligands
Zhou, Zong-Zhou
Liu, Feng-Shou
Shen, Dong-Sheng
Tan, Cheng
Luo, Ling-Yan
INORGANIC CHEMISTRY COMMUNICATIONS, 2011, 14 (05) : 659 - 662
[5] HECK VERSUS SUZUKI PALLADIUM-CATALYZED CROSS-COUPLING OF A VINYLBORONATE ESTER WITH ARYL HALIDES
HUNT, AR
STEWART, SK
WHITING, A
TETRAHEDRON LETTERS, 1993, 34 (22) : 3599 - 3602
[6] An efficient synthesis of 4-substituted coumarin derivatives via a palladium-catalyzed Suzuki cross-coupling reaction
Rajale, Trideep
Sharma, Shikha
Stroud, Daniel A.
Unruh, Daniel K.
Miaou, Emily
Lai, Kimberly
Birney, David M.
TETRAHEDRON LETTERS, 2014, 55 (49) : 6627 - 6630
[7] Diastereoselective synthesis of tetrahydroquinolines via a palladium-catalyzed Heck-Suzuki cascade reaction
Wilson, Jonathan E.
TETRAHEDRON LETTERS, 2012, 53 (18) : 2308 - 2311
[8] Palladium-Catalyzed Cross-Coupling Reaction of Diarylmethanol Derivatives with Diborylmethane
Asai, Kento
Miura, Masahiro
Hirano, Koji
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (11): : 7436 - 7445
[9] Palladium-catalyzed Suzuki cross-coupling reactions in a microemulsion
Vashchenko, Valery
Krivoshey, Alexander
Knyazeva, Irina
Petrenko, Alexey
Goodby, John W.
TETRAHEDRON LETTERS, 2008, 49 (09) : 1445 - 1449
[10] Palladium-catalyzed Heck and Suzuki coupling in glycerol
Wolfson, A.
Dlugy, C.
CHEMICAL PAPERS, 2007, 61 (03): : 228 - 232

← 1 2 3 4 5 →