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

[41] Advance on Applications of Microwave Technique in Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction
Li, Qinghan
Ding, Yong
Zhang, Gang
Zhang, Zhen
Mo, Song
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2016, 36 (01) : 83 - 104
[42] Simultaneous Reduction of Aldehyde Group to Hydroxymethyl Group in Palladium-catalyzed Suzuki Cross-coupling Reaction
Wang Yingchun
Li Xiuying
Li Yajun
Pan Yingming
Cheng Keguang
Wang Hengshan
CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2014, 30 (04) : 614 - 618
[43] One-Pot Palladium-Catalyzed Cross-Coupling Treble of Borylation, the Suzuki Reaction and Amination
Jong, Howard
Eey, Stanley T. -C.
Lim, Yee Hwee
Pandey, Sangeeta
Iqbal, Nurul Azmah Bte
Yong, Fui Fong
Robins, Edward G.
Johannes, Charles W.
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (04) : 616 - 622
[44] Simultaneous reduction of aldehyde group to hydroxymethyl group in palladium-catalyzed Suzuki cross-coupling reaction
Yingchun Wang
Xiuying Li
Yajun Li
Yingming Pan
Keguang Cheng
Hengshan Wang
Chemical Research in Chinese Universities, 2014, 30 : 614 - 618
[45] Efficient Pyrimidone-Promoted Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction
Zhang, Hong-Ping
Dai, You-Zhi
Zhou, Xi
Yu, Huang
SYNLETT, 2012, (08) : 1221 - 1224
[46] Synthesis of (Hetero)Aryl-Functionalized Azaindoline Derivatives by Palladium-Catalyzed Domino Heck Cyclization/Hiyama Cross-Coupling
Ye, Hao
Zhang, Ruotong
Xia, Xiaolong
Ding, Yue
Sun, Meihui
Shi, Lei
Jiang, Guomin
Wu, Xin-Xing
SYNTHESIS-STUTTGART, 2021, 53 (21): : 4079 - 4085
[47] Ligand effects in palladium-catalyzed Suzuki and Heck coupling reactions
Hanhan, M. Emre
APPLIED ORGANOMETALLIC CHEMISTRY, 2008, 22 (05) : 270 - 275
[48] SYNTHESIS OF CLOMID USING PALLADIUM-CATALYZED CROSS-COUPLING
ALHASSAN, MI
SYNTHETIC COMMUNICATIONS, 1987, 17 (15) : 1787 - 1796
[49] SYNTHESIS OF BROPARESTROL USING PALLADIUM-CATALYZED CROSS-COUPLING
ALHASSAN, MI
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 321 (01) : 119 - 121
[50] Palladium-catalyzed cross-coupling reactions in total synthesis
Nicolaou, KC
Bulger, PG
Sarlah, D
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (29) : 4442 - 4489

← 1 2 3 4 5 →