A New Strategy for the Synthesis of Poly-Substituted 3-H, 3-Fluoro, or 3-Trifluoromethyl Pyridines via the Tandem C-F Bond Cleavage Protocol

被引：33

作者：

Chen, Zixian ^{[1
,2
]}

Zhu, Jiangtao ^{[1
]}

Xie, Haibo ^{[1
]}

Li, Shan ^{[1
]}

Wu, Yongming ^{[1
]}

Gong, Yuefa ^{[2
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

[2] Huazhong Univ Sci & Technol, Sch Chem & Chem Engn, Wuhan 430074, Peoples R China

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 19期

基金：

美国国家科学基金会;

关键词：

ONE-POT SYNTHESIS; ANTIBACTERIAL AGENTS; HERBICIDAL ACTIVITY; COUPLING REACTIONS; FACILE SYNTHESIS; DERIVATIVES; AMINOPYRIDINES; DIAZOTIZATION; EFFICIENT; IODIDES;

D O I：

10.1021/ol101859p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new strategy for the synthesis of poly-substituted 3-H, 3-F, and 3-trifluoromethyl pyridines based on C-F bond breaking of the anionically activated fluoroalkyl group is described. A series of 2,6-disubstituted 4-amino pyridines were prepared through this domino process in high yields under noble metal-free conditions, making this method a supplement to pyridine synthesis.

引用

页码：4376 / 4379

页数：4

共 50 条

[1] Selective synthesis of poly-substituted fluorine-containing pyridines and dihydropyrimidines via cascade C-F bond cleavage protocol
Chen, Zixian
Zhu, Jiangtao
Xie, Haibo
Li, Shan
Wu, Yongming
Gong, Yuefa
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (16) : 5682 - 5691
[2] Synthesis and biological activity of substituted 3-fluoro/3-trifluoromethyl 10H-phenothiazines, its ribofuranosides and sulfones
Gautam, Naveen
Goyal, Kshamta
Saini, Omprakash
Kumar, Ashok
Gautam, D. C.
JOURNAL OF FLUORINE CHEMISTRY, 2011, 132 (06) : 420 - 426
[3] Csp3-H monofluoroalkenylation via stereoselective C-F bond cleavage
Hu, Ying
Liu, Xingchen
Ren, Zhouyang
Hu, Binjing
Li, Jie
CHEMICAL COMMUNICATIONS, 2022, 58 (16) : 2734 - 2737
[4] Base-Mediated Regioselective [3+3] Annulation of Alkylidene Malononitriles with Trifluoromethyl Alkenes via Dual C-F Bond Cleavage
Li, Mingqiang
Zeng, Weidi
Abdukader, Ablimit
Wu, Shaofeng
Zhou, Lei
ORGANIC LETTERS, 2024, 26 (35) : 7452 - 7456
[5] Synthesis of 5-Fluoro-dihydroindolizines from Pyrrole-2-acetic Acidsand Trifluoromethyl Alkenes via Dual C-F Bond Cleavage in a CF3 Group
Sun, Zhengchang
Zhou, Lei
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (07): : 4801 - 4812
[6] NHC-catalyzed [4+2] cycloaddition reactions for the synthesis of 3′-spirocyclic oxindoles via a C-F bond cleavage protocol
Yan, Jun
Shi, Kuangxi
Zhao, Chengtao
Ding, Liyuan
Jiang, Shengsheng
Yang, Limin
Zhong, Guofu
CHEMICAL COMMUNICATIONS, 2018, 54 (13) : 1567 - 1570
[7] Transition metal-free synthesis of 3-trifluoromethyl chromones via tandem C-H trifluoromethylation and chromone annulation of enaminones
Yu, Qing
Liu, Yunyun
Wan, Jie-Ping
ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (18) : 2770 - 2775
[8] Synthesis of poly-substituted nitrobenzene derivatives from Baylis-Hillman adducts via [3+3] annulation protocol
Park, Da Yeon
Lee, Ka Young
Kim, Jae Nyoung
TETRAHEDRON LETTERS, 2007, 48 (09) : 1633 - 1636
[9] Partially fluorinated heterocycles from 4,4-bis(trifluoromethyl)-hetero-1,3-dienes via C-F bond activation -: Synthesis of 2-fluoro-3-(trifluoromethyl)furans
Burger, Klaus
Helmreich, Brigitte
Hennig, Lothar
Spengler, Jan
Albericio, Fernando
Fuchs, Annett
MONATSHEFTE FUR CHEMIE, 2007, 138 (03): : 227 - 236
[10] Synthesis of Poly-Substituted Benzene Derivatives via [3+3] Annulation Protocol from Morita-Baylis-Hillman Adducts and Glutaconates
Lim, Jin Woo
Kim, Se Hee
Yu, Jin
Kim, Jae Nyoung
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2013, 34 (11): : 3503 - 3506

← 1 2 3 4 5 →