Desulfonylative Radical Truce-Smiles Rearrangement Utilizing the Benzimidazoline and Benzimidazolium Redox Couple

被引：0

作者：

Miyajima, Ryo ^{[1
]}

Okamura, Manon ^{[1
]}

Oomori, Kazuki ^{[1
]}

Iwamoto, Hajime ^{[1
]}

Wakamatsu, Kan ^{[2
]}

Hasegawa, Eietsu ^{[1
]}

机构：

[1] Niigata Univ, Fac Sci, Dept Chem, 8050 Ikarashi 2,Nishi Ku, Niigata 9502181, Japan

[2] Okayama Univ Sci, Fac Sci, Dept Chem, 1-1 Ridai Cho,Kita Ku, Okayama 7000005, Japan

来源：

SYNLETT | 2024年 / 35卷 / 03期

基金：

日本学术振兴会;

关键词：

benzimidazoline and benzimidazolium redox couple; single-electron transfer; photoreducing catalyst; radical Truce-Smiles rearrangement; desulfonylative aryl migration; PHOTOINDUCED ELECTRON-TRANSFER; TRANSFER PROBES; HYDROGEN-ATOM; LEAVING GROUP; ALPHA; REDUCTION; HYDRIDE; ELECTROCHEMISTRY; TRANSITION; CLEAVAGE;

D O I：

10.1055/a-2153-6594

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed protocols for promoting redox reactions utilizing the 2-substituted 1,3-dimethylbenzimidazoline (BIH-R) and benzimidazolium (BI*-R) couples which were applied to the desulfonylative radical Truce-Smiles rearrangement. Expected rearrangement products formed in modest to good yields in these processes, in which added or in situ generated BIH-R serve as electron-and hydrogen-atom-donating reagents or photocatalysts. DFT calculations were carried out to gain the information about the radical intermediates involved in the rearrangement reaction.

引用

页码：352 / 356

页数：5

共 35 条

[31] PHENYL MIGRATION IN BICYCLO[5.3.1]UNDECA-1,3,5,8-TETRAENE-8-CARBOXY-N-METHYLANILIDE - A UNIQUE TRUCE-SMILES TYPE REARRANGEMENT OF AN ANILIDE
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TETRAHEDRON LETTERS, 1982, 23 (04) : 437 - 438
[32] Accessing chiral sulfones bearing quaternary carbon stereocenters via photoinduced radical sulfur dioxide insertion and Truce–Smiles rearrangement
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Zhiyuan Chen
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Nature Communications, 13
[33] Novel pyrrolo[1,2-a][3.1.6]benzothiadiazocine ring synthesis.: Unusual Truce-Smiles type rearrangement of 1-{[1-(2-nitrophenyl)-1H-pyrrol-2-yl]sulfonyl(or sulfinyl)}acetone
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TETRAHEDRON, 2004, 60 (40) : 8807 - 8815
[34] Polycyclic N-heterocyclic compounds. Part 61: A novel Truce-Smiles type rearrangement reaction of 4-(2-cyanovinyloxy)butanenitriles to give cycloalkeno[1,2-d]furo[2,3-b]pyridines
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TETRAHEDRON LETTERS, 2010, 51 (06) : 903 - 906
[35] Polycyclic N-Heterocyclic Compounds. Part 63 Improved Synthesis of 5-Amino-1,2-dihydrofuro[2,3-c]isoquinolines via Truce-Smiles Rearrangement and Subsequent Formation to Furo[2,3-c]isoquinoline
Okuda, Kensuke
Yoshida, Masahiko
Hirota, Takashi
Sasaki, Kenji
CHEMICAL & PHARMACEUTICAL BULLETIN, 2010, 58 (03) : 363 - 368

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