Chromium-Catalyzed Defluorinative Reductive Coupling of Aldehydes with gem-Difluoroalkenes

被引：6

作者：

Liu, Yu-Tao ^{[1
]}

Fan, Yu-Hang ^{[1
]}

Mei, Yan ^{[1
]}

Li, Dong-Jie ^{[1
]}

Jiang, Yan ^{[1
]}

Yu, Wen-Hao ^{[1
]}

Pan, Fei ^{[1
]}

机构：

[1] Sichuan Normal Univ, Coll Chem & Mat Sci, Chengdu 610068, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 03期

基金：

中国国家自然科学基金;

关键词：

ELECTROORGANIC CHEMISTRY; OLEFINIC KETONES; PHOTOREDOX;

D O I：

10.1021/acs.orglett.3c00016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, a mild and convenient defluorinative reductive cross coupling of gem-difluoroalkenes with aliphatic aldehydes has been developed to afford diverse silyl-protected beta-fluorinated allylic alcohols. The reaction is operationally simple and shows good functional group tolerance with moderate to excellent yields. The utility of this method is demonstrated by converting the products into various bioactive fluorinated compounds, showing its potential applications in drug discovery and biochemistry.

引用

页码：549 / 554

页数：6

共 50 条

[31] Copper(I)-catalyzed Stereoselective Defluoroborylation of Aliphatic Gem-Difluoroalkenes
Ito, Hajime
Seo, Tamae
Kojima, Ryoto
Kubota, Koji
CHEMISTRY LETTERS, 2018, 47 (10) : 1330 - 1332
[32] Cobalt-Catalyzed Selective Unsymmetrical Dioxidation of gem-Difluoroalkenes
Orsi, Douglas L.
Douglas, Justin T.
Sorrentino, Jacob P.
Altman, Ryan A.
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (16): : 10451 - 10465
[33] Stereoselective Palladium-Catalyzed Hiyama Cross-Coupling Reaction of Tetrasubstituted gem-Difluoroalkenes
Li, Min
Tsui, Gavin Chit
ORGANIC LETTERS, 2023, 26 (01) : 376 - 379
[34] Nickel-Catalyzed Enantioselective Hydrosilylation of gem-Difluoroalkenes with Silanes
Chen Jianqiang
Wu Jie
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (03) : 921 - 922
[35] Palladium-Catalyzed Stereoselective Hydrodefluorination of Tetrasubstituted gem-Difluoroalkenes
Ma, Quo
Liu, Caroline
Tsui, Gavin Chit
ORGANIC LETTERS, 2020, 22 (13) : 5193 - 5197
[36] Electrochemical synthesis of functionalized gem-difluoroalkenes with diverse alkyl sources via a defluorinative alkylation process
Zhang, Haoxiang
Liang, Mengze
Zhang, Xiao
He, Meng-Ke
Yang, Chao
Guo, Lin
Xia, Wujiong
ORGANIC CHEMISTRY FRONTIERS, 2021, 9 (01) : 95 - 101
[37] Synthesis of Monofluorocyclohexene via Photocatalytic Defluorinative [4+2] Annulation of gem-Difluoroalkenes with Unactivated Alkenes
Zhang, Guang-Xu
Li, Dong-Sheng
Xue, Fei
Chen, An-Feng
Deng, Hong-Ping
ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (24) : 4603 - 4608
[38] Recent Advances in Transition Metal-catalyzed Functionalization of gem-Difluoroalkenes
Koley, Suvajit
Altman, Ryan A.
ISRAEL JOURNAL OF CHEMISTRY, 2020, 60 (3-4) : 313 - 339
[39] Stereoselective formation of Z-monofluoroalkenes by nickel-catalyzed defluorinative coupling of gem–difluoroalkenes with lithium organoborates
Yisa Xiao
Weichen Huang
Qilong Shen
Chinese Chemical Letters, 2022, 33 (09) : 4277 - 4280
[40] Efficient Decarboxylative/Defluorinative Alkylation for the Synthesis of gem-Difluoroalkenes through an SN2'-Type Route
Xing, Wei-Long
Wang, Jia-Xin
Fu, Ming-Chen
Fu, Yao
CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (03): : 323 - 328

← 1 2 3 4 5 →