Chemical versatility of azide radical: journey from a transient species to synthetic accessibility in organic transformations

Maniklal Shee and N. D. Pradeep Singh

Chem. Soc. Rev., 2022, 51, 2255
DOI: 10.1039/D1CS00494H

Radical selenation of C(sp3)–H bonds to asymmetric selenides and mechanistic study

Xin Wang, Jia Lei, Sa Guo, Yan Zhang, Yong Ye, Shi Tang and Kai Sun

Chem. Commun., 2022, 58, 1526
DOI: 10.1039/D1CC06323E

Transition-metal-, oxidant- and additive-free multi-component synthesis of alkyl heteroaryl BCPs enabled by visible-light-induced phosphine-catalyzed halogen-atom transfer

Jun Xu, Yu Hong, Ruiyuan Xu, Yuxin Wang, Yirui Guo, Jiabin Shen, Yuxuan Zhao and Wanmei Li

Org. Chem. Front., 2024, 11, 6166
DOI: 10.1039/D4QO01351D

Continuous flow synthesis of 1,4-disubstituted 1,2,3-triazoles via consecutive β-azidation of α,β-unsaturated carbonyl compounds and CuAAC reactions

Giulia Brufani, Federica Valentini, Gabriele Rossini, Luigi Carpisassi, Daniela Lanari and Luigi Vaccaro

Green Chem., 2023, 25, 2438
DOI: 10.1039/D2GC04672E

Visible light-inducedgem-difluoroallylation of [1.1.1]propellane to accessgem-difluoroallylic bicyclo[1.1.1]pentanes

Hui Zhu, Shengxing Wu, Bingbin Zhu, Jiacheng Li, Deyou Lan, Wenhao Xu, Gongcheng Xu, Yu Zhu, Chuanming Yu and Xinpeng Jiang

Chem. Commun., 2023, 59, 5213
DOI: 10.1039/D3CC00822C

Synthesis of C3-halo substituted bicyclo[1.1.1]pentylamines via halosulfoamidation of [1.1.1]propellane with sodium hypohalites and sulfonamides

Zhi Li, Deyou Lan, Wei Zhou, Jiacheng Li, Hui Zhu, Chuanming Yu and Xinpeng Jiang

Chem. Commun., 2023, 59, 6056
DOI: 10.1039/D3CC01262J

Sustainable synthesis of 1-thiol-3-alkyl bicyclo[1.1.1]pentanes via electron donor–acceptor complex photoactivation: a metal- and additive-free strategy for bioisostere design

Ruiyuan Xu, Binye Cao, Yibo Wang, Jingyi Zhang, Yuping Huang and Wanmei Li

Green Chem., 2025, 27, 9223
DOI: 10.1039/D5GC02067K

Visible-light-induced direct perfluoroalkylation/heteroarylation of [1.1.1]propellane to diverse bicyclo[1.1.1]pentanes (BCPs) under metal and photocatalyst-free conditions

Jiashun Zhu, Yirui Guo, Yuru Zhang, Wanmei Li, Pengfei Zhang and Jun Xu

Green Chem., 2023, 25, 986
DOI: 10.1039/D2GC04521D

Visible light-induced synthesis of 1,3-disubstituted bicyclo[1.1.1]pentane ketonesviacooperative photoredox and N-heterocyclic carbene catalysis

Yan Gao, Zicong Zheng, Yu Zhu, Wenhao Xu, Yu Zhou, Chuanming Yu and Xinpeng Jiang

Green Chem., 2023, 25, 3909
DOI: 10.1039/D3GC00643C

Photocatalyzed radical multicomponent alkylacylation of [1.1.1]propellane to synthesize 1,3-disubstituted BCP ketones

Yong-Ze Liu, Yan Jiang, Jun-Lei Zhang, Yan Mei, Dong-Jie Li and Fei Pan

Org. Chem. Front., 2023, 10, 4616
DOI: 10.1039/D3QO01019H

Visible-light photoredox-catalyzed three-component radical alkyl-acylation of [1.1.1]propellane

Lanqin Liu, Shengkun Guo, Chengjun Chen, Xiaoyu Shen, Xiaoyun Chen, Huaguang Yu, Ying Han, Qiu Sun, Shaoqun Zhu and Hong Hou

Org. Biomol. Chem., 2024, 22, 9192
DOI: 10.1039/D4OB01549E

Amine-promoted three-component cycloaddition of bicyclo[1.1.0]butanes with hydroxylamine and polyformaldehyde: expedient access to 2-oxa-3-azabicyclo[3.1.1]heptanes

Yu Zhu, Xueli Lv, Jun Hong, Shengxing Wu, Zhi Li, Minyan Wang and Xinpeng Jiang

Green Chem., 2025, 27, 2464
DOI: 10.1039/D4GC05355A

Metal and catalyst-free strategy to access 1,3-thio-heteroaryl BCP derivatives

Surbhi Gupta, Vinjamuri Srinivasu and Devarajulu Sureshkumar

Org. Biomol. Chem., 2023, 21, 8136
DOI: 10.1039/D3OB01377D

Synthesis of tetrasubstituted alkenyl nitriles via cyanocarbene addition of [1.1.1]propellane

Xinpeng Jiang, Zicong Zheng, Yan Gao, Deyou Lan, Wenhao Xu, Wang Zhang and Guofei Chen

Org. Chem. Front., 2022, 9, 2234
DOI: 10.1039/D2QO00186A

Mn-catalyzed oxo-alkylation of 1,2,4-triazine-3,5(2H,4H)-diones with cyclic alkanols via oxidative cross-dehydrogenative coupling

Qianqian Liang, Shuomeng Bai, Yushi Tan, Hong-Yu Zhang, Yuecheng Zhang and Jiquan Zhao

Org. Biomol. Chem., 2025, 23, 4161
DOI: 10.1039/D5OB00098J

PIDA-mediated segment coupling for the synthesis of azido-methyl substituted ketones via 1,5-hydrogen atom transfer (HAT)

Santosh J. Gharpure, Anusha Khandelwal and Rupali S. Chavan

Chem. Commun., 2025, 61, 17161
DOI: 10.1039/D5CC04895H

Synthesis of 1-perfluoroalkyl-3-heteroaryl bicyclo[1.1.1]pentanes via visible light-induced and metal-free perfluoroalkylation of [1.1.1]propellane

Boan Yan, Gongcheng Xu, Hang Han, Jun Hong, Wenhao Xu, Deyou Lan, Chuanming Yu and Xinpeng Jiang

Green Chem., 2023, 25, 1948
DOI: 10.1039/D2GC04683K

Photocatalytic synthesis of 3,3-disubstituted cyclobutanols via trifunctionalization of [1.1.1]propellane

Jiacheng Li, Yue Wang, Yijun Jin, Longyi Li, Guoxiang Bao, Xingyi Zhu and Xinpeng Jiang

Green Chem., 2025, 27, 11510
DOI: 10.1039/D5GC02651B

Three‐Component Reactions of Quinoxalin‐2(1H)‐ones: Recent Advances

Ke‐Li Wang, Hong‐Tao Ji, Li‐Juan Ou and Wei‐Min He

Eur J Org Chem, 2023, 26
DOI: 10.1002/ejoc.202300752

Photocatalytic Difunctionalization of [1.1.1]Propellane

Tanmay Das, Mrittika Mohar and Alakananda Hajra

The Chemical Record, 2025, 25
DOI: 10.1002/tcr.202500018

Self-photocatalyzed three-component radical cascade reaction of quinoxalinones, simple alkenes and zhdankin reagent

Xiao-Yun Sun, Wen-Hao Liu, Xing-Yuan Liu, Wa Gao, Han-Qing Zhao and Zi-Hao Xia

Molecular Catalysis, 2024, 557, 113981
DOI: 10.1016/j.mcat.2024.113981

Multicomponent Synthesis of Alkyl BCP-Heteroaryls via Electron Donor–Acceptor Complex Photoactivation under Mild Conditions

Yanhe Li, Jun Xu, Yuxin Wang, Ruiyuan Xu, Yuxuan Zhao and Wanmei Li

J. Org. Chem., 2025, 90, 1683
DOI: 10.1021/acs.joc.4c02941

Synthesis of Imidized Cyclobutene Derivatives by Strain Release of [1.1.1]Propellane

Xiaofan Du, Di Xu, Gongcheng Xu, Chuanming Yu and Xinpeng Jiang

Org. Lett., 2022, 24, 7323
DOI: 10.1021/acs.orglett.2c02790

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

Xiaobo Dang, Zhixuan Li, Jinlong Shang, Chenyang Zhang, Chao Wang and Zhaoqing Xu

Angew Chem Int Ed, 2024, 63
DOI: 10.1002/anie.202400494

Photoinduced Copper‐Catalyzed Radical Ring‐Opening Azidation of Cyclic Oxime Esters

Li‐Bo Yang, Jia Hu, Tian‐Tian Zou, Xin‐Song Zhou, Jing Li, Yuan Qu and Ya‐Min Li

Adv Synth Catal, 2025, 367
DOI: 10.1002/adsc.70133

Three-Component Strategy for the Synthesis of Alkyl Nitrile BCP Derivatives

Jiabin Shen, Lin Li, Qing Pang, Liang-Feng Yang, Kai Ge, Chao Shen and Pengfei Zhang

J. Org. Chem., 2025, 90, 9223
DOI: 10.1021/acs.joc.5c01224

Direct Diazoarylation of [1.1.1]Propellane with Arenediazonium Salts: A Modular Assembly of Arylated Diazo Bicyclo[1.1.1]pentanes

Hailing Nan, Beiyi Cheng, Duo Zhang, Kaiping Wang, Shuli Wang, Bingxin Xu, Shuwei Zhang, Burkhard König and Guodong Zhang

Org. Lett., 2024, 26, 8424
DOI: 10.1021/acs.orglett.4c03316

Diverse Synthesis of Azoles: Construction of ortho‐Azidotetrazoles/Triazoletetrazoles through N−N Cleavage of 2H‐Indazoles

Sudip Laru, Suvam Bhattacharjee and Alakananda Hajra

Adv Synth Catal, 2025, 367
DOI: 10.1002/adsc.202401423

Photocatalytic Three-Component Synthesis of 3-Heteroarylbicyclo[1.1.1]pentane-1-acetates

Wenhao Xu, Zicong Zheng, Guoxiang Bao, Yue Wang, Yan Gao, Hui Zhu, Gongcheng Xu, Yu Zhu, Chuanming Yu and Xinpeng Jiang

Org. Lett., 2023, 25, 4050
DOI: 10.1021/acs.orglett.3c01213

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

Xiaobo Dang, Zhixuan Li, Jinlong Shang, Chenyang Zhang, Chao Wang and Zhaoqing Xu

Angewandte Chemie, 2024, 136
DOI: 10.1002/ange.202400494

Multicomponent Radical Cross‐Coupling Reaction of [1.1.1]Propellane: Synthesis of 1‐Arylthiol‐3‐Heteroaryl Bicyclo[1.1.1]pentanes †

Lin Li, Yumiao Liu, Jian Li, Qing Chen, Pengfei Zhang, Jiabin Shen and Jirong Wu

Adv Synth Catal, 2023, 365, 3112
DOI: 10.1002/adsc.202300534

Visible Light‐Induced Sulfonamidation of [1.1.1]Propellane Promoted by Energy Transfer Catalysis

Deyou Lan, Wei Zhou, Zhi Li, Yue Wang, Longyi Li, Wenhao Xu, Hui Zhu, Gongcheng Xu, Yu Zhu and Xinpeng Jiang

Chemistry A European J, 2025, 31
DOI: 10.1002/chem.202501164

Photocatalyzed 1,3-Bromodifluoroallylation of [1.1.1]Propellane with α-Trifluoromethylalkenes and KBr Salts

Kaiping Wang, Beiyi Cheng, Burkhard König, Duo Zhang, Bingxin Xu, Shuli Wang and Guodong Zhang

Org. Lett., 2024, 26, 6889
DOI: 10.1021/acs.orglett.4c02476

Photocatalytic Diheteroarylation of [1.1.1]Propellane for the Construction of 1,3-Diheteroaryl Bicyclo[1.1.1]pentanes

Guoxiang Bao, Yue Wang, Wenhao Xu, Zhihao Yu, Wei Zhou, Jiacheng Li, Longyi Li and Xinpeng Jiang

Org. Lett., 2024, 26, 9210
DOI: 10.1021/acs.orglett.4c03198

Photoinduced Metal‐/Additive‐Free Difluoromethylation of N‐Heteroaromatics†

Congjun Zhu, Yangyang Shen, Tao Guo, Qing Yang, Dongpu Zhao, Huiqing Yang and Jin Xie

Chin. J. Chem., 2025, 43, 905
DOI: 10.1002/cjoc.202401153

Photoredox/Copper Cooperatively Catalyzed Arylalkynylation of [1.1.1]Propellane

Huifang Ma, Duo Zhang, Beiyi Cheng, Lei Wang, Bingxin Xu, Shuli Wang, Shuwei Zhang, Jiahang Lv, Burkhard König and Guodong Zhang

Org. Lett., 2025, 27, 3446
DOI: 10.1021/acs.orglett.5c00882

Synthesis of Azo-Substituted Bicyclo[1.1.1]pentanes (BCPs) via Base-Promoted Halogen Atom Transfer

Yanchuang Zhao, Jing Zhang, Zhi-Jin Zhan, Qiujin Fan, Xu-Qiong Xiao, Ying Bai, Shao-Fei Ni and Xinxin Shao

Org. Lett., 2024, 26, 4406
DOI: 10.1021/acs.orglett.4c01546