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.
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页数：4
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