gem-Bromonitroalkane Involved Radical 1,2-Aryl Migration of ?,?- Diaryl Allyl Alcohol TMS Ether via Visible-Light Photoredox Catalysis

被引：6

作者：

Ma, Shanshan ^{[1
]}

Guo, Yawen ^{[1
]}

Liu, Lidong ^{[1
]}

Shi, Lin ^{[1
]}

Lei, Xingyu ^{[1
]}

Duan, Xinfang ^{[1
]}

Jiao, Peng ^{[1
]}

机构：

[1] Beijing Normal Univ, Coll Chem, Beijing 100875, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 07期

关键词：

TRIFLUOROMETHYLATION; ARYL; ARYLTRIFLUOROMETHYLATION; FUNCTIONALIZATION; REARRANGEMENT; ALKENES;

D O I：

10.1021/acs.joc.3c00343

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and efficient coupling method concerning the reactions of gem-bromonitroalkanes with alpha,alpha-diaryl allyl alcohol trimethylsilyl ethers was reported. A cascade consisting of visible light-induced generation of an alpha-nitroalkyl radical and a subsequent neophyl-type rearrangement was key to realize the coupling reactions. Structurally diverse alpha-aryl-gamma-nitro ketones, especially those bearing a nitrocyclobutyl structure, were prepared in moderate to high yields, which could be converted into spirocyclic nitrones and imines.

引用

页码：4743 / 4756

页数：14

共 9 条

[1] Polychloromethylation-Initiated Radical 1,2-Aryl Migration of α,α-Diarylallyl Alcohols via Visible-Light Photoredox Catalysis
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[2] Alkylation/1,2-aryl migration of α-aryl allylic alcohols with α-carbonyl alkyl bromides using visible-light photoredox catalysis
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[3] Carbotrifluoromethylation of Allylic Alcohols via 1,2-Aryl Migration Promoted by Visible-Light-Induced Photoredox Catalysis
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[7] Visible light-mediated NHC and photoredox co-catalyzed 1,2-sulfonylacylation of allenes via acyl and allyl radical cross-coupling
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[8] Expanding Reaction Profile of Allyl Carboxylates via 1,2-Radical Migration (RaM): Visible-Light-Induced Phosphine-Catalyzed 1,3-Carbobromination of Allyl Carboxylates
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