Silver(I)-Catalyzed Enyne Cyclization/Aromatization of Alkyne-Tethered Cyclohexadienones to Access Meta-Substituted Phenols

被引：16
作者：
Munakala, Anandarao [1 ,2 ]
Chegondi, Rambabu [1 ,2 ]
机构：
[1] CSIR Indian Inst Chem Technol CSIR IICT, Dept Organ Synth & Proc Chem, Hyderabad 500007, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 02期
关键词：
CATALYZED AEROBIC DEHYDROGENATION; C-O BOND; HYDROXYLATION; OXYGENATION; DERIVATIVES; 1,6-ENYNES; OXIDATION; ARYLATION; ROUTE; CYCLOISOMERIZATION;
D O I：
10.1021/acs.orglett.0c03819
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein we report a highly regioselective silver(I)-catalyzed intramolecular annulation of alkyne-tethered cyclohexadienones to access meta-substituted phenols with enone functionality, which are difficult to synthesize from conventional methods. The reaction proceeds via intramolecular 1,6-enyne cyclization followed by aromatization and subsequent oxetene ring rearrangement. This strategy has also been compatible with a wide range of C-tethered cyclohexadienones to afford indanes in high yields. The unique functionality of products allows further transformations to expand the diversity.
引用
收藏
页码：317 / 323
页数：7
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