Synthesis of aminoalkyl nitriles through 2-azaallyl-anion-driven cascade radical ring-opening/intermolecular coupling

Yonggang Jiang, Cuirong Qin, Haoqin Tang, Liang Li, Hongbin Zhang and Xiaodong Yang

Org. Chem. Front., 2026, 13, 408
DOI: 10.1039/D5QO01353D

Strain-release 2-azaallyl anion addition/borylation of [1.1.1]propellane: synthesis and functionalization of benzylamine bicyclo[1.1.1]pentyl boronates

Russell A. Shelp, Anthony Ciro, Youge Pu, Rohan R. Merchant, Jonathan M. E. Hughes and Patrick J. Walsh

Chem. Sci., 2021, 12, 7066
DOI: 10.1039/D1SC01349A

α-Branched amines through radical coupling with 2-azaallyl anions, redox active esters and alkenes

Shengzu Duan, Yujin Zi, Lingling Wang, Jielun Cong, Wen Chen, Minyan Li, Hongbin Zhang, Xiaodong Yang and Patrick J. Walsh

Chem. Sci., 2022, 13, 3740
DOI: 10.1039/D2SC00500J

Intramolecular cyclization of N-aryl amides for the synthesis of 3-amino oxindoles

Haitao Yang, Yu Pan, Yijing Tian, Kaili Yu, Yifeng Bai, Yonggang Jiang, Hongbin Zhang, Guogang Deng and Xiaodong Yang

Chem. Commun., 2024, 60, 14125
DOI: 10.1039/D4CC05259E

Efficient construction of functionalized pyrroloindolines through cascade radical cyclization/intermolecular coupling

Yonggang Jiang, Dongxiang Liu, Lening Zhang, Cuirong Qin, Hui Li, Haitao Yang, Patrick J. Walsh and Xiaodong Yang

Chem. Sci., 2024, 15, 2205
DOI: 10.1039/D3SC05210A

Visible-light-driven net-1,2-hydrogen atom transfer of amidyl radicals to access β-amido ketone derivatives

Yonggang Jiang, Hui Li, Haoqin Tang, Qingyue Zhang, Haitao Yang, Yu Pan, Chenggang Zou, Hongbin Zhang, Patrick J. Walsh and Xiaodong Yang

Chem. Sci., 2025, 16, 962
DOI: 10.1039/D4SC04997G

Design and Synthesis of Fluorescent 1,3-Diaryl-β-carbolines and 1,3-Diaryl-3,4-dihydro-β-carbolines

JiYang Pu, Biao Chen, Wanhua Wu, Cheng Yang, Guoqing Zhang and Jason J. Chruma

ACS Omega, 2021, 6, 12238
DOI: 10.1021/acsomega.1c01116

Synthesis of 4-Pyrrolin-3-ones via the 5-endo-trig Cyclization of Conjugated 2-Azaallyl Radicals

Anastasiya V. Agafonova, Alexander F. Khlebnikov and Mikhail S. Novikov

Org. Lett., 2025, 27, 8229
DOI: 10.1021/acs.orglett.5c02379

Catalytic Chemo‐ and Regioselective Radical Carbocyanation of 2‐Azadienes for the Synthesis of α‐Amino Nitriles

Shengzu Duan, Ya Du, Lingling Wang, Xun Tian, Yujin Zi, Hongbin Zhang, Patrick J. Walsh and Xiaodong Yang

Angew Chem Int Ed, 2023, 62
DOI: 10.1002/anie.202300605

Critical Assessment of the Reducing Ability of Breslow‐type Derivatives and Implications for Carbene‐Catalyzed Radical Reactions**

Ludivine Delfau, Samantha Nichilo, Florian Molton, Julie Broggi, Eder Tomás‐Mendivil and David Martin

Angew Chem Int Ed, 2021, 60, 26783
DOI: 10.1002/anie.202111988

C–F Bond Functionalization: Controlled Didefluorination of o-Trifluoromethyl Benzylamines

Siddhant A. Kale, Rushikesh R. Kusmude, Mahesh Kumar Ravva, Mahipal Yadav and Seema Dhiman

Org. Lett., 2025, 27, 9270
DOI: 10.1021/acs.orglett.5c02828

Catalytic Dehydrogenative β-Alkylation of Amino Acid Schiff Bases with Hydrocarbon

Tetsu Ikeda, Haruka Ochiishi, Mana Yoshida, Ryo Yazaki and Takashi Ohshima

Org. Lett., 2022, 24, 369
DOI: 10.1021/acs.orglett.1c04042

Catalytic Chemo‐ and Regioselective Radical Carbocyanation of 2‐Azadienes for the Synthesis of α‐Amino Nitriles

Shengzu Duan, Ya Du, Lingling Wang, Xun Tian, Yujin Zi, Hongbin Zhang, Patrick J. Walsh and Xiaodong Yang

Angewandte Chemie, 2023, 135
DOI: 10.1002/ange.202300605

Benzylic C(sp3)–H/C(sp3)–H Coupling with 2-Azaallyl Anions through Single-Electron Transfer and 1,5-Hydrogen Atom Transfer

Dongxiang Liu, Bijun Wang, Cuirong Qin, Haoqing Tang, Hui Li, Liang Li, Yonggang Jiang and Xiaodong Yang

Org. Lett., 2025, 27, 3054
DOI: 10.1021/acs.orglett.5c00708

Copper-Catalyzed β-Functionalization of Amino Acid Schiff Bases

Haruka Ochiishi, Kengo Todaka, Yuri Tabuchi, Takashi Ohshima and Ryo Yazaki

Org. Lett., 2025, 27, 12974
DOI: 10.1021/acs.orglett.5c03895

Transition-metal-free allylation of 2-azaallyls with allyl ethers through polar and radical mechanisms

Guogang Deng, Shengzu Duan, Jing Wang, Zhuo Chen, Tongqi Liu, Wen Chen, Hongbin Zhang, Xiaodong Yang and Patrick J. Walsh

Nat Commun, 2021, 12
DOI: 10.1038/s41467-021-24027-6

Mechanistic Study on Copper-Catalyzed C(sp3)–H Alkylation of Amino Acid Schiff Bases for Synthesis of Highly Congested Unnatural α-Amino Acids

Jiali Peng and Dongju Zhang

J. Org. Chem., 2026, 91, 4601
DOI: 10.1021/acs.joc.5c02980

Influence of sp2 Nitrogen Atom Replacement on the Structure and Redox Properties of Allylic Intermediates

Yu-Hua Guo and Ming-Tian Zhang

J. Org. Chem., 2025, 90, 9014
DOI: 10.1021/acs.joc.5c00690

Synthesis of Tryptamines from Radical Cyclization of 2-Iodoaryl Allenyl Amines and Coupling with 2-Azallyls

Bo Wang, Minyan Li, Gui Gao, Alvaro Sanz-Vidal, Bing Zheng and Patrick J. Walsh

J. Org. Chem., 2022, 87, 8099
DOI: 10.1021/acs.joc.2c00767

Recent Advances in Radical Coupling Strategies Enabled by 2‐Azaallyl Anions as Super‐Electron‐Donors

Dong Zou., Wei Wang and Jie Ying

Adv Synth Catal, 2024, 366, 1450
DOI: 10.1002/adsc.202301436

Organic Bases as the Organic Electron Donors (OED) Promoted Reductive Coupling of Diarylhalomethanes: Halogens Controlled Construction of Tetraarylethylenes and Tetraarylethanes

Tong Li, Jie Mao, Shuwei Zhang, Qiyuan Ma, Yuqin Chen, Yu Yuan and Xiaodong Jia

J. Org. Chem., 2024, 89, 13101
DOI: 10.1021/acs.joc.4c01219

Iodoarene Activation: Take a Leap Forward toward Green and Sustainable Transformations

Toshifumi Dohi, Elghareeb E. Elboray, Kotaro Kikushima, Koji Morimoto and Yasuyuki Kita

Chem. Rev., 2025, 125, 3440
DOI: 10.1021/acs.chemrev.4c00808

Super-Electron-Donor 2-Azaallyl Anions Enable Construction of Isoquinolines

Quanxing Zi, Minyan Li, Jielun Cong, Guogang Deng, Shengzu Duan, Meng Yin, Wen Chen, Hong Jing, Xiaodong Yang and Patrick J. Walsh

Org. Lett., 2022, 24, 1786
DOI: 10.1021/acs.orglett.2c00140

α-Amino acid and peptide synthesis using catalytic cross-dehydrogenative coupling

Taro Tsuji, Kayoko Hashiguchi, Mana Yoshida, Tetsu Ikeda, Yunosuke Koga, Yusaku Honda, Tsukushi Tanaka, Suyong Re, Kenji Mizuguchi, Daisuke Takahashi, Ryo Yazaki and Takashi Ohshima

Nat. Synth, 2022, 1, 304
DOI: 10.1038/s44160-022-00037-0

Single-Electron Reduction of “Push–Pull” C–C Single Bond and Decyanation Using Tertiary Amines as the Organic Electron Donor

Tong Li, Zheng Sun, Shuwei Zhang, Qiyuan Ma, Yuqin Chen, Yu Yuan and Xiaodong Jia

J. Org. Chem., 2024, 89, 2516
DOI: 10.1021/acs.joc.3c02542

Synthesis of gem-Difluorohomoallyl Amines via a Transition-Metal-Free Defluorinative Alkylation of Benzyl Amines with Trifluoromethyl Alkenes

Man Ren, Shengjiao Yu, Xuefeng Li, Wenlong Yuan, Ji Lu, Ying Xiong, Hongliang Liu, Jun Wang and Jun Wei

J. Org. Chem., 2024, 89, 8342
DOI: 10.1021/acs.joc.4c00084

α‐Difluoroalkylation of Benzyl Amines with Trifluoromethylarenes

Wen‐Jun Yue and Ruben Martin

Angewandte Chemie, 2023, 135
DOI: 10.1002/ange.202310304

SET activation of nitroarenes by 2-azaallyl anions as a straightforward access to 2,5-dihydro-1,2,4-oxadiazoles

Dong Zou, Lishe Gan, Fan Yang, Huan Wang, Youge Pu, Jie Li and Patrick J. Walsh

Nat Commun, 2021, 12
DOI: 10.1038/s41467-021-26767-x

Critical Assessment of the Reducing Ability of Breslow‐type Derivatives and Implications for Carbene‐Catalyzed Radical Reactions**

Ludivine Delfau, Samantha Nichilo, Florian Molton, Julie Broggi, Eder Tomás‐Mendivil and David Martin

Angewandte Chemie, 2021, 133, 26987
DOI: 10.1002/ange.202111988

Dual NHC/HAT‐Promoted Esterification to Access α‐Aryl Glycines

Matthew J. McGill, Adam X. Wayment, Cullen R. Schull and Karl A. Scheidt

Adv Synth Catal, 2025, 367
DOI: 10.1002/adsc.202401207

α‐Difluoroalkylation of Benzyl Amines with Trifluoromethylarenes

Wen‐Jun Yue and Ruben Martin

Angew Chem Int Ed, 2023, 62
DOI: 10.1002/anie.202310304

Sulfonamides as N-Centered Radical Precursors for C–N Coupling Reactions To Generate Amidines

Guogang Deng, Zhuo Chen, Yifeng Bai, Lening Zhang, Dazhen Xia, Shengzu Duan, Wen Chen, Hongbin Zhang, Patrick J. Walsh and Xiaodong Yang

Org. Lett., 2024, 26, 3855
DOI: 10.1021/acs.orglett.4c01014

Net-1,2-Hydrogen Atom Transfer of Amidyl Radicals: Toward the Synthesis of 1,2-Diamine Derivatives

Yonggang Jiang, Dongxiang Liu, Madeline E. Rotella, Guogang Deng, Zhengfen Liu, Wen Chen, Hongbin Zhang, Marisa C. Kozlowski, Patrick J. Walsh and Xiaodong Yang

J. Am. Chem. Soc., 2023, 145, 16045
DOI: 10.1021/jacs.3c04376