Dearomatization/Spiroannulation of Halophenols Enables the Forging of Contiguous Quaternary Carbon Cyclohexadienones

Dong, Sichan1; Fu, Changzhen1; Ge, Yicong1,2,3; Liu, Jingjing1; Wang, Han1; Luan, Xinjun1

2023-10-20

10.1021/acs.orglett.3c03035

ORGANIC LETTERS   影响因子和分区

1523-7060

1523-7052

A dearomatization/spiroannulation process has been successfully achieved between simple halophenols and alpha,beta-unsaturated olefins under mild reaction conditions. This transformation addresses the chemoselectivity issue in the dearomatizative transformation of phenol scaffolds (6 pi-electron) caused by the SEAr process, enabling the construction of versatile cyclohexadienone frameworks containing contiguous quaternary all-carbon centers in high yields. Further studies have provided valuable insights into the process, revealing that debromination/spiroannulation occurs through the S(RN)1 pathway.

SCI ; IC ; CCR

英语

NI论文

其他

National Natural Science Foundation of China["22171225","22201230","21925108"] ; Shaanxi Fundamental Science Research Project for Chemistry Biology[22JHZ001]

Chemistry

Chemistry, Organic

WOS:001098794500001

AMER CHEMICAL SOC

CHEMISTRY

Web of Science

1.Northwest Univ, Coll Chem & Mat Sci, Key Lab Synthet & Nat Funct Mol, Minist Educ, Xian 710127, Peoples R China
2.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Guangdong, Peoples R China
3.Southern Univ Sci & Technol, Dept Chem, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Guangdong, Peoples R China

Dong, Sichan,Fu, Changzhen,Ge, Yicong,et al. Dearomatization/Spiroannulation of Halophenols Enables the Forging of Contiguous Quaternary Carbon Cyclohexadienones[J]. ORGANIC LETTERS,2023,25(43).

Dong, Sichan,Fu, Changzhen,Ge, Yicong,Liu, Jingjing,Wang, Han,&Luan, Xinjun.(2023).Dearomatization/Spiroannulation of Halophenols Enables the Forging of Contiguous Quaternary Carbon Cyclohexadienones.ORGANIC LETTERS,25(43).

Dong, Sichan,et al."Dearomatization/Spiroannulation of Halophenols Enables the Forging of Contiguous Quaternary Carbon Cyclohexadienones".ORGANIC LETTERS 25.43(2023).