Photoinduced C(sp3)-H Bicyclopentylation Enabled by an Electron Donor-Acceptor Complex-Mediated Chemoselective Three-Component Radical Relay

被引:16
|
作者
Dang, Xiaobo [1 ]
Li, Zhixuan [1 ]
Shang, Jinlong [1 ]
Zhang, Chenyang [1 ]
Wang, Chao [1 ,2 ,3 ]
Xu, Zhaoqing [1 ,2 ]
机构
[1] Lanzhou Univ, Sch Basic Med Sci, Key Lab Preclin Study New Drugs Gansu Prov, 199 West Donggang Rd, Lanzhou 730000, Peoples R China
[2] Chinese Acad Med Sci, Res Unit Peptide Sci, 2019RU066, 199 West Donggang Rd, Lanzhou 730000, Peoples R China
[3] Lanzhou Univ, Technol & Engn Inst, Gongyuan Rd, Baiyin 730900, Peoples R China
基金
中国国家自然科学基金;
关键词
electron donor-acceptor complex; radical relay; bicyclo[1.1.1]pentanes; C(sp(3))-H functionalization; GLYCINE RESIDUES; STRATEGIES;
D O I
10.1002/anie.202400494
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The photoredox electron donor-acceptor (EDA) complex-mediated radical coupling reaction has gained prominence in the field of organic synthesis, finding widespread application in two-component coupling reactions. However, EDA complex-promoted multi-component reactions are not well developed with only a limited number of examples have been reported. Herein, we report a photoinduced and EDA complex-promoted highly chemoselective three-component radical arylalkylation of [1.1.1]propellane, which allows the direct functionalization of C(sp(3))-H with bicyclo[1.1.1]pentanes (BCP)-aryl groups under mild conditions. A variety of unnatural alpha-amino acids, featuring structurally diversified 1,3-disubstituted BCP moieties, were synthesized in a single-step process. Notably, leveraging the high tension release of [1.1.1]propellane, the highly unstable transient aryl radical undergoes rapid conversion into a relatively stable tertiary alkyl transient radical, and consequently, the competing side-reaction of two-component coupling was entirely suppressed. The strategic use of this transient radical conversion approach would be useful for the design of diverse EDA complex-mediated multi-component reactions. It is noteworthy that the highly chemoselective late-stage incorporation of the 1,3-disubstituted BCP pharmacophores into peptides was achieved both in liquid-phase and solid-phase reactions. This advancement is anticipated to have significant application potential in the future development of peptide drugs.
引用
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页数:9
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