Transition-metal-free decarbonylative alkylation towards N-aryl α-hydroxy amides via triple C–C bond cleavages and their selective deuteration

Chengyu Sun, Yang Yu, Xiao Zhang, Yonghai Liu, Chengtao Sun, Guoyin Kai, Lei Shi and Hao Li

Org. Chem. Front., 2021, 8, 4814
DOI: 10.1039/D1QO00530H

Copper-catalyzed decarboxylative stereospecific amidation of cinnamic acids with N-fluorobenzenesulfonimide

Daoshan Yang, Mingyang Sun, Wei Wei, Jin Li, Pengfei Sun, Qingyun Zhang, Laijin Tian and Hua Wang

RSC Adv., 2016, 6, 72361
DOI: 10.1039/C6RA16115D

Copper-catalyzed direct monofluoroalkenylation of C(sp3)–H bondsviadecarboxylation of α-fluoroacrylic acids

Xiao-Yu Lu, Xing-Ke Chen, Meng-Ting Gao, Xiao-Mei Sun, Run-Chuang Jiang, Jun-Chao Wang, Li-Juan Yu, Meng-Yuan Ge, Zheng-Huan Wei and Zi Liu

Org. Chem. Front., 2022, 9, 4712
DOI: 10.1039/D2QO00977C

Highly regioselective para-methylthiolation/bridging methylenation of arylamines promoted by NH4I

Yinfeng Xu, Tiantian Cong, Ping Liu and Peipei Sun

Org. Biomol. Chem., 2015, 13, 9742
DOI: 10.1039/C5OB01679G

BPO-promoted direct oxidative C–H functionalization of unactivated alkanes into 6-alkyl-6H-benzo[c]chromenes under transition-metal-free conditions

Lei Ji, Qinfei Deng, Ping Liu and Peipei Sun

Org. Biomol. Chem., 2019, 17, 7715
DOI: 10.1039/C9OB01396B

Free-radical anti-Markovnikov hydroalkylation of unactivated alkenes with simple alkanes

Yunfei Tian, Anbo Ling, Ren Fang, Ren Xiang Tan and Zhong-Quan Liu

Green Chem., 2018, 20, 3432
DOI: 10.1039/C8GC01394B

Direct radical functionalization methods to access substituted adamantanes and diamondoids

William K. Weigel, Hoang T. Dang, Abigail Feceu and David B. C. Martin

Org. Biomol. Chem., 2022, 20, 10
DOI: 10.1039/D1OB01916C

Metal- and photosensitizer-free cross-dehydrogenative coupling through photoinduced energy transfer

Bo Liu, Qiong Wang, Bin Cheng, Taimin Wang, Hongze Liao and Hou-Wen Lin

Green Chem., 2024, 26, 4742
DOI: 10.1039/D3GC03983H

Transition metal-free decarboxylative alkylation reactions

Ping Liu, Guanghui Zhang and Peipei Sun

Org. Biomol. Chem., 2016, 14, 10763
DOI: 10.1039/C6OB02101H

Copper-catalyzed radical cascade oxyalkylation of olefinic amides with simple alkanes: highly efficient access to benzoxazines

Jie Wang, Ruoyu Sang, Xiaolong Chong, Yinuo Zhao, Wenjie Fan, Zejiang Li and Jincan Zhao

Chem. Commun., 2017, 53, 7961
DOI: 10.1039/C7CC04213B

Decarboxylative reactions with and without light – a comparison

Johanna Schwarz and Burkhard König

Green Chem., 2018, 20, 323
DOI: 10.1039/C7GC02949G

Decarboxylative functionalization of cinnamic acids

Arun Jyoti Borah and Guobing Yan

Org. Biomol. Chem., 2015, 13, 8094
DOI: 10.1039/C5OB00727E

C–H functionalisation of cycloalkanes

Arghya Banerjee, Satavisha Sarkar and Bhisma K. Patel

Org. Biomol. Chem., 2017, 15, 505
DOI: 10.1039/C6OB01975G

Copper-catalyzed oxidative decarboxylative alkylation of cinnamic acids with 4-alkyl-1,4-dihydropyridines

Dong Zhang, Zi-Liang Tang, Xuan-Hui Ouyang, Ren-Jie Song and Jin-Heng Li

Chem. Commun., 2020, 56, 14055
DOI: 10.1039/D0CC06401G

Boosting free radical type photocatalysis over Pd/Fe-MOFs by coordination structure engineering

Hongmei Cheng, Cuicui Zang, Fengxia Bian, Yanke Jiang, Lin Yang, Fan Dong and Heyan Jiang

Catal. Sci. Technol., 2021, 11, 5543
DOI: 10.1039/D1CY00972A

Copper‐Catalyzed C(sp3)−H α‐Acetylation: Generation of Quaternary Centers

Otome E. Okoromoba, Ting‐An Chen, Eun Sil Jang, Claire L. McMullin, Thomas R. Cundari and Timothy H. Warren

Angew Chem Int Ed, 2025, 64
DOI: 10.1002/anie.202418692

Annulation of 1-(2-Aminoaryl)pyrroles, Ethers with Elemental Sulfur To Give 1,3,6-Benzothiadiazepine Derivatives through Double C–S Bond Formation and C–O Cleavage of Ethers

Jie Zhang, Chuwen Song, Linfeng Sheng, Ping Liu and Peipei Sun

J. Org. Chem., 2019, 84, 2191
DOI: 10.1021/acs.joc.8b03187

Catalyst‐ and Additive‐Free Decarboxylative C‐4 Phosphorylation of Coumarin‐3‐Carboxylic Acids at Ambient Conditions

Goutam Brahmachari

Adv Synth Catal, 2020, 362, 5411
DOI: 10.1002/adsc.202001054

Advances in Decarboxylative Oxidative Coupling Reaction

Tong Zhang, Nai-Xing Wang and Yalan Xing

J. Org. Chem., 2018, 83, 7559
DOI: 10.1021/acs.joc.8b01080

Iron-Catalyzed Decarboxylative Olefination of Unstrained Carbon–Carbon Bonds Relying on Alkoxyl Radical Induced Cascade

Pin Gao, Hao Wu, Jun-Cheng Yang and Li−Na Guo

Org. Lett., 2019, 21, 7104
DOI: 10.1021/acs.orglett.9b02675

A Regioselective Metal-Free Construction of 3-Aroyl Coumarins by Csp2-H Functionalization

Farnaz Jafarpour and Masoumeh Abbasnia

J. Org. Chem., 2016, 81, 11982
DOI: 10.1021/acs.joc.6b02051

Recent Advances of Cinnamic Acids in Organic Synthesis

Lihua Chen, Ling Zhang, Guobing Yan and Dayun Huang

Asian J Org Chem, 2020, 9, 842
DOI: 10.1002/ajoc.202000217

Visible‐Light‐Mediated Dual Decarboxylative Coupling of Redox‐Active Esters with α,β‐Unsaturated Carboxylic Acids

Jin‐Jiang Zhang, Jun‐Cheng Yang, Li‐Na Guo and Xin‐Hua Duan

Chemistry A European J, 2017, 23, 10259
DOI: 10.1002/chem.201702200

Photoredox Reaction of 2-Mercaptothiazolinium Salts with Silyl Enol Ethers

Artem A. Zemtsov, Salavat S. Ashirbaev, Vitalij V. Levin, Vladimir A. Kokorekin, Alexander A. Korlyukov and Alexander D. Dilman

J. Org. Chem., 2019, 84, 15745
DOI: 10.1021/acs.joc.9b02478

Iron-Catalyzed Decarboxylative Olefination of Cycloketone Oxime Esters with α,β-Unsaturated Carboxylic Acids via C–C Bond Cleavage

Jing-Feng Zhao, Xin-Hua Duan, Yu-Rui Gu, Pin Gao and Li-Na Guo

Org. Lett., 2018, 20, 4614
DOI: 10.1021/acs.orglett.8b01901

Cyanomethylation and Cyclization of Aryl Alkynoates with Acetonitrile under Transition-Metal-Free Conditions: Synthesis of 3-Cyanomethylated Coumarins

Yulan Yu, Shengyi Zhuang, Ping Liu and Peipei Sun

J. Org. Chem., 2016, 81, 11489
DOI: 10.1021/acs.joc.6b02155

Oxidative difunctionalization of alkynoates via cascade radical addition, aryl migration, and decarboxylation

Changduo Pan, Honglin Zhang and Chengjian Zhu

Tetrahedron Letters, 2016, 57, 595
DOI: 10.1016/j.tetlet.2015.12.092

Metal‐Free Decarboxylation of α,β‐Unsaturated Carboxylic Acids for Carbon–Carbon and Carbon–Heteroatom Coupling Reactions

Xianjun Xu, Erik V. Van der Eycken and Huangdi Feng

Chin. J. Chem., 2020, 38, 1780
DOI: 10.1002/cjoc.202000326

Acetonitrile-dependent oxyphosphorylation: A mild one-pot synthesis of β-ketophosphonates from alkenyl acids or alkenes

Xi Chen, Xiaolan Chen, Xu Li, Chen Qu, Lingbo Qu, Wenzhu Bi, Kai Sun and Yufen Zhao

Tetrahedron, 2017, 73, 2439
DOI: 10.1016/j.tet.2017.03.026

Cu(II) Promoted C(sp3)−H Activation in Unactivated Cycloalkanes: Oxo‐Alkylation of Styrenes to Synthesize β‐Disubstituted Ketones

Krishna Mohan Das, Adwitiya Pal, Lakshmi Surya T, Lisa Roy and Arunabha Thakur

Chemistry A European J, 2024, 30
DOI: 10.1002/chem.202303776

Dealkenylative Alkenylation: Formal σ‐Bond Metathesis of Olefins

Manisha Swain, Gusein Sadykhov, Ruoxi Wang and Ohyun Kwon

Angewandte Chemie, 2020, 132, 17718
DOI: 10.1002/ange.202005267

1,4‐Dioxane as Precursor of −CH2CH2−: A Simple and Convenient Strategy to Synthesize 1,2‐Disulfide Substituted Ethanes Initiated by Iodine

Yufeng Liu, Wentao Xie, Zhen Wei, Lili Geng, Cengceng Du and Xiaoning Shen

Eur J Org Chem, 2025, 28
DOI: 10.1002/ejoc.202401143

Metal-Free Decarboxylative Cyanomethylation of β-Aryl/Heteroaryl Substituted α,β-Unsaturated Carboxylic Acids to γ-Ketonitriles

Shiv Chand, Saurabh Kumar, Anup Kumar Sharma and Krishna Nand Singh

Org. Lett., 2024, 26, 10051
DOI: 10.1021/acs.orglett.4c03994

Recent advances in decarboxylative C-C bond formation using direct or in situ generated alkenyl acids

Pavneet Kaur, Vinod Kumar and Rakesh Kumar

Catalysis Reviews, 2020, 62, 118
DOI: 10.1080/01614940.2019.1700736

Transition-Metal-Free C–P Bond Formation via Decarboxylative Phosphorylation of Cinnamic Acids with P(O)H Compounds

Lixin Liu, Dan Zhou, Jianyu Dong, Yongbo Zhou, Shuang-Feng Yin and Li-Biao Han

J. Org. Chem., 2018, 83, 4190
DOI: 10.1021/acs.joc.8b00187

Facile photochemical synthesis of α-ketoamides and quinoxalines from amines and benzoylacetonitrile under mild conditions

Chao Zhou, Pinhui Diao, Xiaoji Li, Yanqin Ge and Cheng Guo

Chinese Chemical Letters, 2019, 30, 371
DOI: 10.1016/j.cclet.2018.06.019

Dealkenylative Alkenylation: Formal σ‐Bond Metathesis of Olefins

Manisha Swain, Gusein Sadykhov, Ruoxi Wang and Ohyun Kwon

Angew Chem Int Ed, 2020, 59, 17565
DOI: 10.1002/anie.202005267

Copper‐Catalyzed C(sp3)−H α‐Acetylation: Generation of Quaternary Centers

Otome E. Okoromoba, Ting‐An Chen, Eun Sil Jang, Claire L. McMullin, Thomas R. Cundari and Timothy H. Warren

Angewandte Chemie, 2025, 137
DOI: 10.1002/ange.202418692

Phosphine‐Free Pincer Ruthenium‐Catalyzed α‐Alkylation of Ketones with Secondary Alcohols to form β‐Branched Ketones

Dipanjan Bhattacharyya, Priyanka Adhikari, Nitumoni Hazarika, Bikash Kumar Sarmah and Animesh Das

ChemCatChem, 2023, 15
DOI: 10.1002/cctc.202300542

Synthesis of Trifluoromethylthiolated Alkenes and Ketones by Decarboxylative Functionalization of Cinnamic Acids

Shen Pan, Yangen Huang and Feng‐Ling Qing

Chemistry An Asian Journal, 2016, 11, 2854
DOI: 10.1002/asia.201601098

ChemInform Abstract: Peroxide Promoted Tunable Decarboxylative Alkylation of Cinnamic Acids to Form Alkenes or Ketones under Metal‐Free Conditions.

Jing Ji, Ping Liu and Peipei Sun

ChemInform, 2015, 46
DOI: 10.1002/chin.201534072

Recent Advances in Radical C–H Activation/Radical Cross-Coupling

Hong Yi, Guoting Zhang, Huamin Wang, Zhiyuan Huang, Jue Wang, Atul K. Singh and Aiwen Lei

Chem. Rev., 2017, 117, 9016
DOI: 10.1021/acs.chemrev.6b00620

Iron(III)‐Catalyzed Peroxide‐Mediated C‐3 Functionalization of Flavones

Bilal Ahmad Mir, Arghya Banerjee, Sourav Kumar Santra, Suresh Rajamanickam and Bhisma K. Patel

Adv Synth Catal, 2016, 358, 3471
DOI: 10.1002/adsc.201600565

Decarboxylative Alkylcarboxylation of α,β-Unsaturated Acids Enabled by Copper-Catalyzed Oxidative Coupling

Bao Gao, Yinjun Xie, Zhiqiang Shen, Lei Yang and Hanmin Huang

Org. Lett., 2015, 17, 4968
DOI: 10.1021/acs.orglett.5b02382

Photoinduced copper-catalyzed dual decarboxylative coupling of α,β-unsaturated carboxylic acids with redox-active esters

Xiao-Yu Lu, Ang Gao, Qi-Le Liu and Ze-Jie Xia

Tetrahedron, 2021, 92, 132259
DOI: 10.1016/j.tet.2021.132259

Transition-Metal-Free Oxidative Decarboxylative Cross Coupling of α,β-Unsaturated Carboxylic Acids with Cyclic Ethers under Air Conditions: Mild Synthesis of α-Oxyalkyl Ketones

Peng-Yi Ji, Yu-Feng Liu, Jing-Wen Xu, Wei-Ping Luo, Qiang Liu and Can-Cheng Guo

J. Org. Chem., 2017, 82, 2965
DOI: 10.1021/acs.joc.6b02993

Copper(II)-catalyzed decarboxylative cyclization for accessing biologically relevant 3-(2-furanyl) Indoles via 3-cyanoacetyl indoles and cinnamic acids

Abhishek Kumar, Sarita Katiyar, Ruchir Kant and Koneni V. Sashidhara

Tetrahedron, 2020, 76, 131433
DOI: 10.1016/j.tet.2020.131433

Photoinduced, Copper-Promoted Regio- and Stereoselective Decarboxylative Alkylation of α,β-Unsaturated Acids with Alkyl Iodides

Chao Wang, Yingjie Lei, Mengzhun Guo, Qinyu Shang, Hong Liu, Zhaoqing Xu and Rui Wang

Org. Lett., 2017, 19, 6412
DOI: 10.1021/acs.orglett.7b03289

Merging Photoredox and Copper Catalysis: Enantioselective Radical Cyanoalkylation of Styrenes

Wanxing Sha, Lingling Deng, Shengyang Ni, Haibo Mei, Jianlin Han and Yi Pan

ACS Catal., 2018, 8, 7489
DOI: 10.1021/acscatal.8b01863

Recent Advances in Di-tert-butyl Peroxide (DTBP)-Promoted C-C Bond Formation Reactions

Ravi Varala, Kamsali Murali Mohan Achari, Mohamed Hussein and Mohammed Mujahid Alam

MROC, 2025, 22, 590
DOI: 10.2174/0118756298333423241022033447

Microwave‐Promoted Metal‐Free α‐Alkylation of Ketones with Cycloalkanes through Cross‐Coupling of C(sp3)−H Bonds

Qian‐Qian Wang, Zhang‐Xin Wang, Xin‐Ying Zhang and Xue‐Sen Fan

Asian J Org Chem, 2017, 6, 1445
DOI: 10.1002/ajoc.201700256

Unactivated C(sp3)–H Bond Functionalization of Alkyl Nitriles with Vinylarenes and Mechanistic Studies

Xing-Wang Lan, Nai-Xing Wang, Cui-Bing Bai, Cui-Lan Lan, Tong Zhang, Shi-Lu Chen and Yalan Xing

Org. Lett., 2016, 18, 5986
DOI: 10.1021/acs.orglett.6b02692

Visible Light-Mediated Photocatalytic Metal-Free Cross-Coupling Reaction of Alkenyl Carboxylic Acids with Diarylphosphine Oxides Leading to β-Ketophosphine Oxides

Hai-Feng Qian, Cheng-Kun Li, Zhi-Hao Zhou, Ze-Kun Tao, Adedamola Shoberu and Jian-Ping Zou

Org. Lett., 2018, 20, 5947
DOI: 10.1021/acs.orglett.8b02639

Cobalt-Catalyzed Oxyalkylation Reaction of Styrenes: Rapid Access to α-Alkyl Substituted Acetophenone Derivatives

Peng Zhou, Weiming Zhu, Jiantao Zhang, Duoduo Xiao, Xiangfeng Guo and Weibing Liu

Chinese Journal of Organic Chemistry, 2023, 43, 3939
DOI: 10.6023/cjoc202304010

Design and synthesis of the basic Cu-doped zeolite X catalyst with high activity in oxidative coupling reactions

Shengchun Chen, Zhen Shao, Zhongxue Fang, Qun Chen, Ting Tang, Wenqian Fu, Lei Zhang and Tiandi Tang

Journal of Catalysis, 2016, 338, 38
DOI: 10.1016/j.jcat.2016.01.030

Energy-Transfer Excitation of Dibenzothiophene S-Oxide Induces Oxomethylation of Styrenes

Saki Maejima, Ban Kinoshita, Ryota Wakabayashi, Manabu Abe and Hideki Yorimitsu

Org. Lett., 2025, 27, 11678
DOI: 10.1021/acs.orglett.5c03852

I2/TBHP Reagent System: A Modern Paradigm for Organic Transformations**

Nancy Slathia, Annah Gupta and Kamal K. Kapoor

Eur J Org Chem, 2022, 2022
DOI: 10.1002/ejoc.202200460

Site-Selective C–H Functionalization by Decatungstate Anion Photocatalysis: Synergistic Control by Polar and Steric Effects Expands the Reaction Scope

Davide Ravelli, Maurizio Fagnoni, Takahide Fukuyama, Tomohiro Nishikawa and Ilhyong Ryu

ACS Catal., 2018, 8, 701
DOI: 10.1021/acscatal.7b03354

One‐Pot Synthesis of Indolizines Using TBHP as the Methylene Source Under Metal‐Free Condition

Qianwei Zhang, Keyume Ablajan, Bin Wang, Huifang Ma and Zhongqi Guo

Eur J Org Chem, 2020, 2020, 262
DOI: 10.1002/ejoc.201901803