Gold(I)-Catalyzed [2+2] and [3+2] Cycloadditions of 1,1-Difluoroallenes with Aldehydes: Switchable Syntheses of Fluorinated Oxetanes and Furans

被引：0

作者：

Miyazaki, Daisuke ^{[1
]}

Kudo, Konami ^{[1
]}

Fujiki, Yusuke ^{[1
]}

Watanabe, Natsumi ^{[1
]}

Matsui, Toru ^{[1
]}

Ichikawa, Junji ^{[2
]}

Fuchibe, Kohei ^{[1
]}

机构：

[1] Univ Tsukuba, Fac Pure & Appl Sci, Div Chem, Tsukuba, Ibaraki 3058571, Japan

[2] Sagami Chem Res Inst, Ayase, Kanagawa 2521193, Japan

来源：

ORGANIC LETTERS | 2025年

基金：

日本学术振兴会;

关键词：

CATALYTIC CYCLOADDITIONS; EFFICIENT ACCESS; GOLD; COMPLEXES; ALLENAMIDES; REACTIVITY; ALLENES; ALKYNES;

D O I：

10.1021/acs.orglett.4c04185

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,1-Difluoroallenes underwent regioselective [2 + 2] and [3 + 2] cycloadditions with aldehydes using Au(I) catalysts. An AuCl catalyst enabled an alpha,beta-selective [2 + 2] cycloaddition of 1,1-difluoroallenes, yielding (E)-3-alkylidene-2,2-difluorooxetanes. Conversely, an AuCl(IPr)-AgSbF6 catalyst facilitated an alpha,gamma-selective [3 + 2] cycloaddition, followed by dehydrofluorination to produce aromatized 2-fluorofurans. DFT calculations (B3LYP level) suggested that the former reaction proceeded through Au(III)-containing metallacycles, while the latter involved cyclic Au(I) carbenoids.

引用

页数：6

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