Photoinduced stereoselective hydroalkylation of terminal arylalkynes via C(sp3)-H functionalization

被引：4

作者：

Liu, Fen ^{[1
]}

Zhang, Kun ^{[3
]}

Zhao, Xiao-Fei ^{[1
]}

Meng, Qing-Xin ^{[1
]}

Zhao, Tian-Sheng ^{[1
]}

Tian, Wan-Fa ^{[2
]}

He, Yong-Qin ^{[1
]}

机构：

[1] Nanchang Univ, Sch Pharmaceut Sci, Nanchang 330006, Peoples R China

[2] Jiangxi Sci & Technol Normal Univ, Key Lab Organ Chem Jiangxi Prov, Nanchang 330013, Peoples R China

[3] Jiangxi Acad Emergency Management Sci, Nanchang 330030, Peoples R China

来源：

TETRAHEDRON LETTERS | 2023年 / 115卷

关键词：

C(sp3)-H functionalization; Photoinduced reaction; Hydroalkylation of alkynes; Electron catalysis; C-H BONDS; PHOTOREDOX CATALYSIS; RADICAL REACTIONS; C(SP(3))-H BONDS; ALKYNES; ELECTRON; ALKENYLATION; ACTIVATION; ACIDS;

D O I：

10.1016/j.tetlet.2022.154321

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A photoinduced stereoselective hydroalkylation of terminal arylalkynes via C(sp3)-H activation was developed. This method employed an organic dye 2,4,5,6-tetrakis(carbazol-9-yl)-1,3 dicyanobenzene (4CzIPN) as photosensitizer and N-hydroxyphthalimide (NHPI) as the HAT catalyst, which totally inhib-ited the usage of transition metals and stoichimetrical oxidant or radical initiators (e.g. TBHP). The method also displayed good functional tolerance, allowing access to 1,2-disubstituted alkenes in (Z) -major stereo-selectivity. Primary mechanism studies suggested that the reaction proceed via an elec-tron-catalyzed process. (c) 2022 Elsevier Ltd. All rights reserved.

引用

页数：4

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