Visible Light-Induced Divergent Deoxygenation/Hydroxymethylation of Pyridine N-Oxides

被引：1

作者：

Feng, Changhao ^{[1
]}

Guo, Hao ^{[1
]}

Ding, Aishun ^{[1
]}

机构：

[1] Fudan Univ, Dept Chem, Shanghai 200438, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2025年 / 90卷 / 03期

关键词：

C-H-ARYLATION; EFFICIENT DEOXYGENATION; HYDROXYMETHYLATION; SULFOXIDES; CONSTRUCTION; CATALYST; DRUGS; WATER; ACIDS;

D O I：

10.1021/acs.joc.4c02770

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This study explores the deoxygenation of pyridine N-oxides and presents a one-step photoredox method for the direct synthesis of 2-hydroxymethylated pyridines from pyridine N-oxides. Mechanism studies elucidate the role of the catalyst and provide evidence of the possible electron transfer process and the formation of key radicals. A range of pyridine derivatives, particularly 2-hydroxymethyl-substituted pyridines, which may be difficult to obtain, can be synthesized in a single step.

引用

页码：1376 / 1387

页数：12

共 50 条

[21] Electrochemical Deoxygenation of N-Heteroaromatic N-Oxides
Xu, P.
Xu, H. -C.
SYNLETT, 2019, 30 (10) : 1219 - 1221
[22] An efficient deoxygenation of nitrones and heteroarene N-oxides
Dutta, DK
Konwar, D
JOURNAL OF CHEMICAL RESEARCH-S, 1998, (05): : 266 - +
[23] DEOXYGENATION OF QUINOXALINE N-OXIDES AND RELATED COMPOUNDS
HADDADIN, MJ
ZAHR, GE
RAWDAH, TN
CHELHOT, NC
ISSIDORI.CH
TETRAHEDRON, 1974, 30 (05) : 659 - 666
[24] DEOXYGENATION OF AROMATIC N-OXIDES WITH SULFUR MONOCHLORIDE
BEGUM, S
SHAKIR, N
PAKISTAN JOURNAL OF SCIENTIFIC AND INDUSTRIAL RESEARCH, 1974, 17 (06) : 198 - 199
[25] A NEW METHOD FOR DEOXYGENATION OF AROMATIC N-OXIDES
ABRAMOVI.R
ADAMS, KAH
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1961, 39 (10): : 2134 - &
[26] PHOTOINDUCED DEOXYGENATION REACTION OF HETEROCYCLIC N-OXIDES
HATA, N
ONO, I
KAWASAKI, M
CHEMISTRY LETTERS, 1975, (01) : 25 - 28
[27] THE PHOTO-DEOXYGENATION OF HETEROCYCLIC N-OXIDES
FASANI, E
AMER, AM
ALBINI, A
HETEROCYCLES, 1994, 37 (02) : 985 - 992
[28] CHEMOSELECTIVE DEOXYGENATION OF NITRONES AND N-OXIDES WITH TETRATHIOMOLYBDATE
ILANKUMARAN, P
CHANDRASEKARAN, S
TETRAHEDRON LETTERS, 1995, 36 (27) : 4881 - 4882
[29] A NEW TYPE OF DEOXYGENATION OF QUINOXALINE N-OXIDES
KURASAWA, Y
KATOH, R
KUREYAMA, T
YOSHISHIBA, N
TAKADA, A
KIM, HS
OKAMOTO, Y
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1992, 29 (06) : 1649 - 1651
[30] Catalytic Deoxygenation of Amine and Pyridine N-Oxides Using Rhodium PCcarbeneP Pincer Complexes Hendrik
Tinnermann, Hendrik
Sung, Simon
Cala, Beatrice A.
Gill, Hashir J.
Young, Rowan D.
ORGANOMETALLICS, 2020, 39 (06) : 797 - 803

← 1 2 3 4 5 →