Organophotocatalytic dearomatization of indoles, pyrroles and benzo(thio)furans via a Giese-type transformation

Zhang, Yueteng1,2,3,4,5; Ji, Peng1,2,3,4,5; Gao, Feng1,2,3,4,5; Dong, Yue1,2,3,4,5; Huang, He6; Wang, Changqing1,2,3,4,5; Zhou, Ziyuan7; Wang, Wei1,2,3,4,5

2021-02-19

10.1038/s42004-021-00460-y

Communications Chemistry   影响因子和分区

2399-3669

["Dearomatisation of indoles allows efficient access to indolines, but often is incompatible with electron-withdrawing substituents. Here a photoredox Giese-type dearomatisation of indoles yields 2,3-disubstituted indolines bearing electron-withdrawing groups.","Accessing fascinating organic and biological significant indolines via dearomatization of indoles represents one of the most efficient approaches. However, it has been difficult for the dearomatization of the electron deficient indoles. Here we report the studies leading to developing a photoredox mediated Giese-type transformation strategy for the dearomatization of the indoles. The reaction has been implemented for chemoselectively breaking indolyl C=C bonds embedded in the aromatic system. The synthetic power of this strategy has been demonstrated by using structurally diverse indoles bearing common electron-withdrawing groups including (thio)ester, amide, ketone, nitrile and even aromatics at either C-2 or C-3 positions and ubiquitous carboxylic acids as radical coupling partner with high trans-stereoselectivity (>20:1 dr). This manifold can also be applied to other aromatic heterocycles including pyrroles, benzofurans and benzothiophenes. Furthermore, enantioselective dearomatization of indoles has been achieved by a chiral camphorsultam auxiliary with high diastereoselectivity."]

SCI

英语

其他

Foundation for Basic and Applied Research of Guangdong Province[2019A1515110489]

Chemistry

Chemistry, Multidisciplinary

WOS:000621098300001

NATURE RESEARCH

Web of Science

1.Univ Arizona, Dept Pharmacol, Tucson, AZ 85721 USA
2.Univ Arizona, Dept Toxicol, Tucson, AZ 85721 USA
3.Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
4.Univ Arizona, Dept Biochem, Tucson, AZ 85721 USA
5.Univ Arizona, BIO5 Inst, Tucson, AZ 85721 USA
6.Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY USA
7.Southern Univ Sci & Technol, Hosp 2, Shenzhen Peoples Hosp 3, Natl Clin Res Ctr Infect Dis, Shenzhen, Peoples R China

Zhang, Yueteng,Ji, Peng,Gao, Feng,et al. Organophotocatalytic dearomatization of indoles, pyrroles and benzo(thio)furans via a Giese-type transformation[J]. Communications Chemistry,2021,4(1).

Zhang, Yueteng.,Ji, Peng.,Gao, Feng.,Dong, Yue.,Huang, He.,...&Wang, Wei.(2021).Organophotocatalytic dearomatization of indoles, pyrroles and benzo(thio)furans via a Giese-type transformation.Communications Chemistry,4(1).

Zhang, Yueteng,et al."Organophotocatalytic dearomatization of indoles, pyrroles and benzo(thio)furans via a Giese-type transformation".Communications Chemistry 4.1(2021).