Umpolung of 4,4-disubstituted 2-hydroxycyclohexa-2,5-dienones for the regiodivergent synthesis of disubstituted catechols

被引：0

作者：

Akazawa, Ryunosuke ^{[1
]}

Mohamed, Ahmed A. B. ^{[1
,2
]}

Yahata, Kenzo ^{[1
]}

Miyagaki, Kohei ^{[1
]}

Togami, Masaki ^{[1
]}

Sawama, Yoshinari ^{[1
]}

Kanomata, Kyohei ^{[1
]}

Akai, Shuji ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

[2] Mansoura Univ, Fac Pharm, Dept Med Chem, Mansoura 35516, Dakahlia, Egypt

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 2024年 / 97卷 / 11期

关键词：

catechols; hypervalent iodine reagent; rearrangement; POLYCYCLIC AROMATIC-HYDROCARBONS; DERIVATIVES; QUINONES;

D O I：

10.1093/bulcsj/uoae111

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The umpolung of 4,4-disubstituted 2-hydroxycyclohexa-2,5-dienones 1 with PhI(OCOCF3)(2) achieved the migration into the more electron-rich C3 position, providing exclusively 3,4-disubstituted catechols 3. Acid-induced rearrangement of 1 produced 4,5-disubstituted catechols 2. These two reactions enabled the highly selective production of two regioisomers of disubstituted catechols, especially biaryls containing catechol moieties, from the common intermediates 1.

引用

页数：6

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