A Sterically Tuned 2-Fluoropyridinium Salt for the Catalyst-Free, Visible-Light-Mediated Deoxygenation of Alcohols via an Electron Donor-Acceptor Complex

被引：0

作者：

Nanjo, Takeshi ^{[1
]}

Lin, Yixuan ^{[1
]}

Fujii, Yusei ^{[1
]}

Takemoto, Yoshiji ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Kyoto 6068501, Japan

来源：

ORGANIC LETTERS | 2025年

关键词：

ARYLATION; REDUCTION; OXALATES;

D O I：

10.1021/acs.orglett.5c00266

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We here report the use of a sterically tuned 2-fluoro-1-methylpyridinium salt for the catalyst-free, visible-light-mediated deoxygenative transformation of alcohols through alkoxypyridinium intermediates. The key to this process is the introduction of a bulky cyclohexyl group at the 3-position of the pyridinium ring, which enforces a favorable conformation for C-O bond cleavage and the formation of an electron donor-acceptor complex between the pyridinium ring and amines.

引用

页数：6

共 48 条

[21] Visible light-promoted, photocatalyst-free decarboxylative alkylation of 2H-indazoles via electron donor-acceptor complex activation
Wang, Jin
Song, Qingyuan
He, Xing
Ma, Chunhua
Jiang, Yuqin
Fan, Jing
NEW JOURNAL OF CHEMISTRY, 2022, 46 (34) : 16436 - 16439
[22] Visible-Light-Driven Synthesis of Aryl Xanthates and Aryl Dithiocarbamates via an Electron Donor-Acceptor Complex
Zhang, Mingjun
Wang, Beibei
Cao, Yunpeng
Liu, Yuxiu
Wang, Ziwen
Wang, Qingmin
ORGANIC LETTERS, 2022, 24 (48) : 8895 - 8900
[23] Visible-light-mediated regioselective ring-opening hydrogenolysis of donor-acceptor cyclopropanes with DIPEA and H2O
Liu, Zhen
Wei, Yin
Shi, Min
ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (07): : 1960 - 1966
[24] Visible-light-mediated direct C3-arylation of 2H-indazoles enabled by an electron-donor-acceptor complex
Aganda, Kim Christopher C.
Kim, Junyoung
Lee, Anna
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (45) : 9698 - 9702
[25] Catalyst-Free C(sp2)-H Borylation through Aryl Radical Generation from Thiophenium Salts via Electron Donor-Acceptor Complex Formation
Li, Bo
Wang, Ke
Yue, Huifeng
Drichel, Alwin
Lin, Jingjing
Su, Zhenying
Rueping, Magnus
ORGANIC LETTERS, 2022, 24 (40) : 7434 - 7439
[26] Visible-Light-Promoted C3-Sulfenylindoles with Arylsulfonyl Chlorides via Electron Donor-Acceptor Complex
Xue, Ziqian
Yang, Wenjing
Huang, Qiuzhan
Zhou, Cong-Ying
Guo, Zhen
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (11): : 7591 - 7597
[27] Visible light-driven α-sulfonylation of ketone-derived silyl enol ethers via an electron donor-acceptor complex
Saxena, Barakha
Patel, Roshan I.
Sharma, Anuj
GREEN CHEMISTRY, 2024, 26 (23) : 11650 - 11661
[28] Visible-light activation of a Ru(II) complex catalyst via a carbazole-modified donor-acceptor ligand for CO2 reduction
Nakada, Akinobu
Tomiura, Yuya
Suzuki, Hajime
Tomita, Osamu
Abe, Ryu
CHEMISTRY LETTERS, 2024, 53 (07)
[29] Visible-Light-Induced Deaminative Thioesterification of Amino Acid Derived Katritzky Salts via Electron Donor-Acceptor Complex Formation
Yang, Mingcheng
Cao, Tianpeng
Xu, Tianxiao
Liao, Saihu
ORGANIC LETTERS, 2019, 21 (21) : 8673 - 8678
[30] Transition-Metal-Free and Photocatalyst-Free Sulfenylation of Halopyrazolamines under Visible-Light Irradiation via Electron Donor-Acceptor Complexes
Shanthi, Markabandhu
Perumal, Karuppaiah
Sivalingam, Soumya
Puhazhendhi, Arulmozhi
Kumar Mandali, Pavan
Ramesh, Subburethinam
SYNLETT, 2024, 35 (03) : 313 - 318

← 1 2 3 4 5 →