Direct photo-induced reductive Heck cyclization of indoles for the efficient preparation of polycyclic indolinyl compounds

Yu, Daohong1,2,3; To, Wai-Pong2; Liu, Yungen1; Wu, Liang-Liang2; You, Tingjie2; Ling, Jesse5; Che, Chi-Ming1,2,4,5

2021-09-01

10.1039/d1sc04258k

Chemical Science   影响因子和分区

2041-6520

2041-6539

The photo-induced cleavage of C(sp(2))-Cl bonds is an appealing synthetic tool in organic synthesis, but usually requires the use of high UV light, photocatalysts and/or photosensitizers. Herein is described a direct photo-induced chloroarene activation with UVA/blue LEDs that can be used in the reductive Heck cyclization of indoles and without the use of a photocatalyst or photosensitizer. The indole compounds examined display room-temperature phosphorescence. The photochemical reaction tolerates a panel of functional groups including esters, alcohols, amides, cyano and alkenes (27 examples, 50-88% yields), and can be used to prepare polycyclic compounds and perform the functionalization of natural product analogues in moderate to good yields. Mechanistic experiments, including time-resolved absorption spectroscopy, are supportive of photo-induced electron transfer between the indole substrate and DIPEA, with the formation of radical intermediates in the photo-induced dearomatization reaction.

SCI ; EI

英语

NI论文

第一 ; 通讯

Guangdong Major Project of Basic and Applied Basic Research[2019B030302009] ; Science, Technology and Innovation Commission of Shenzhen Municipality[JCYJ20180508162429786] ; China Postdoctoral Science Foundation[2018M633043]

Chemistry

Chemistry, Multidisciplinary

WOS:000701958600001

ROYAL SOC CHEMISTRY

20214511139315

Absorption spectroscopy ; Amides ; Cyclization ; Free radical reactions ; Photochemical reactions ; Photosensitizers ; Reaction intermediates

Light/Optics:741.1 ; Chemical Reactions:802.2 ; Chemical Products Generally:804 ; Organic Compounds:804.1

Web of Science

1.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Guangdong, Peoples R China
2.Univ Hong Kong, Dept Chem, HKU CAS Joint Lab New Mat, State Key Lab Synthet Chem, Pokfulam Rd, Hong Kong, Peoples R China
3.Gannan Normal Univ, Key Lab Organopharmaceut Chem Jiangxi Prov, Ganzhou 341000, Peoples R China
4.HKU Shenzhen Inst Res & Innovat, Shenzhen 518057, Guangdong, Peoples R China
5.Lab Synthet Chem & Chem Biol Ltd, Units 1503-1511,15-F,Bldg 17W,Hong Kong Sci Pk, Hong Kong, Peoples R China

Yu, Daohong,To, Wai-Pong,Liu, Yungen,et al. Direct photo-induced reductive Heck cyclization of indoles for the efficient preparation of polycyclic indolinyl compounds[J]. Chemical Science,2021,12:14050-14058.

Yu, Daohong.,To, Wai-Pong.,Liu, Yungen.,Wu, Liang-Liang.,You, Tingjie.,...&Che, Chi-Ming.(2021).Direct photo-induced reductive Heck cyclization of indoles for the efficient preparation of polycyclic indolinyl compounds.Chemical Science,12,14050-14058.

Yu, Daohong,et al."Direct photo-induced reductive Heck cyclization of indoles for the efficient preparation of polycyclic indolinyl compounds".Chemical Science 12(2021):14050-14058.