Recent developments in 1,6-addition reactions of para-quinone methides (p-QMs)

Jia-Yin Wang, Wen-Juan Hao, Shu-Jiang Tu and Bo Jiang

Org. Chem. Front., 2020, 7, 1743
DOI: 10.1039/D0QO00387E

Visible-light-promoted radical cross-coupling of para-quinone methides with N-substituted anilines: an efficient approach to 2,2-diarylethylamines

Qiao-Lei Wu, Jing Guo, Gong-Bin Huang, Albert S. C. Chan, Jiang Weng and Gui Lu

Org. Biomol. Chem., 2020, 18, 860
DOI: 10.1039/C9OB02600B

Metal-free synthesis of triarylated (Z)-nitrones via H2O-mediated 1,3-dipolar transfer under aerobic conditions

Ke Chen, Wen-Juan Hao, Shu-Jiang Tu and Bo Jiang

Green Chem., 2019, 21, 675
DOI: 10.1039/C8GC03593H

A one-pot synthesis of 2,3-dihydrobenzofurans, benzofuran-2(3H)-ones, and indoles via a [4 + 1] annulation reaction of ortho-substituted para-quinone methides and bromonitromethane

Amol T. Savekar, Vishal B. Karande, Dattatray G. Hingane and Suresh B. Waghmode

Org. Biomol. Chem., 2024, 22, 8945
DOI: 10.1039/D4OB01369G

Recent progress in the application of iodonium ylides in organic synthesis

Xia Mi, Chao Pi, Weisheng Feng and Xiuling Cui

Org. Chem. Front., 2022, 9, 6999
DOI: 10.1039/D2QO01332K

One-pot synthesis of indoles and quinolinones from ortho-tosylaminophenyl-substituted para-quinone methides

Junwei Wang, Xiang Pan, Quanjin Rong, Lei Zhao, Lin Zhao, Weichen Dai, Kun Zhao and Lihong Hu

RSC Adv., 2020, 10, 33455
DOI: 10.1039/D0RA05497F

1,6-Addition of vinyl p-quinone methides with cyclic sulfamidate imines: access to 4-hydroxyaryl-2,6-diarylpyridines

Soumitra Guin, Santosh K. Gudimella and Sampak Samanta

Org. Biomol. Chem., 2020, 18, 1337
DOI: 10.1039/C9OB02708D

Organocatalytic enantioselective synthesis of dihydronaphthofurans and dihydrobenzofurans: reaction development and insights into stereoselectivity

Zeynep Dilşad Susam, Bilge Deniz Özcan, Enis Kurtkaya, Erol Yildirim and Cihangir Tanyeli

Org. Biomol. Chem., 2022, 20, 8725
DOI: 10.1039/D2OB01571D

A [4 + 1] annulation of ortho-electrophile-substituted para-quinone methides for the synthesis of indanes and isoindolines

Ziwen Feng, Zhenbo Yuan, Xiaobin Zhao, Yue Huang and Hequan Yao

Org. Chem. Front., 2019, 6, 3535
DOI: 10.1039/C9QO00977A

Synthesis of N-functionalized 2,3-disubstituted benzofurans/naphthofurans from para-quinone methides and isocyanides via the [4 + 1] annulation pathway

Someshwar B. Kale, Manish Kumar, Dinesh R. Shinde, Gamidi Rama Krishna and Utpal Das

Org. Chem. Front., 2023, 10, 3746
DOI: 10.1039/D3QO00048F

Rh(iii)-catalyzed cascade annulation reaction of N,N-dimethyl enaminones with iodonium ylides to give substituted isocoumarins

Mingshuai Zhang, Longkun Chen, Donghan Liu, Zhuoyuan Liu, Jiuzhong Huang, Xiang Li and Fuchao Yu

New J. Chem., 2023, 47, 12274
DOI: 10.1039/D3NJ02073H

Asymmetric synthesis of spiro-structural 2,3-dihydrobenzofuransviathe bifunctional phosphonium salt-promoted [4 + 1] cyclization ofortho-quinone methides with α-bromoketones

Song Zhang, Xiaojun Yu, Jianke Pan, Chunhui Jiang, Hongsu Zhang and Tianli Wang

Org. Chem. Front., 2019, 6, 3799
DOI: 10.1039/C9QO01096C

DBU-Promoted Cascade Synthesis of Dihydrocoumarins from p-Quinone Methides and o-Hydroxy Aldimines

Yingpeng Su, Qinqin Ling, Caixia Yang, Zhengang Han, Haiyang He, Shufang Zhang, Jinjin Chang, Xiaolong Zhao, Congde Huo and Xiaolei Wang

J. Org. Chem., 2026, 91, 2404
DOI: 10.1021/acs.joc.5c02600

NEt3-Promoted Construction of Functionalized 4H-Chromenes via [4+2] Cycloaddition Reaction of ortho-Quinone Methides with β-Ketothioamides

Guangming Nan, Jingbo Zhan, Chunming Yuan, Lirong Wen and Ming Li

Chinese Journal of Organic Chemistry, 2021, 41, 3682
DOI: 10.6023/cjoc202104005

Diastereodivergent formal [4 + 1] cycloaddition of azoalkenes as one-carbon synthons

Chun-Yan Guan, Tian-Jiao Han, Shi-Kun Jia, Yuan-Zhao Hua and Guang-Jian Mei

Green Synthesis and Catalysis, 2023, 4, 258
DOI: 10.1016/j.gresc.2022.05.003

Tf2NH catalyzed 1,6‐conjugate addition of 2‐hydroxy‐p‐quinone methides with β‐Functionalized Ketones: Access to 2,3,4,9‐Tetrahydro‐1H‐xanthenones and 4H‐Chromene Derivatives

Shruti Satbhaiya, Nilesh S. Khonde, Jayant Rathod, Rajesh Gonnade and Pradeep Kumar

Eur J Org Chem, 2019, 2019, 3127
DOI: 10.1002/ejoc.201900370

Merging [2+2] Cycloaddition with 1,6‐/1,4‐Aza‐Binucleophilic Additions toward Unprecedented Indazole‐Containing Polycycles

Bu‐Zheng Tang, Jia‐Zhuo Li, Ai‐Wen Zhang, Wen‐Juan Hao, Shu‐Jiang Tu and Bo Jiang

Adv Synth Catal, 2019, 361, 3394
DOI: 10.1002/adsc.201900401

Construction of Oxygen‐ and Nitrogen‐based Heterocycles from p‐Quinone Methides

Gurdeep Singh, Rajat Pandey, Yogesh A. Pankhade, Shaheen Fatma and Ramasamy Vijaya Anand

The Chemical Record, 2021, 21, 4150
DOI: 10.1002/tcr.202100137

Regioselective synthesis of spirobarbiturate-dihydrofurans and dihydrofuro[2,3-d]pyrimidines via one-pot cascade reaction of barbiturate-based olefins and ethyl acetoacetate

Songtao Liu, Pei Shao, Yanli Li, Donghao Wang, Deshan Hou, Chaofan Qu, Xixi Song and Xuebin Yan

Tetrahedron, 2021, 79, 131859
DOI: 10.1016/j.tet.2020.131859

Enantioselective Synthesis of Triarylmethanes via Organocatalytic 1,6‐Addition of Arylboronic Acids to para‐Quinone Methides

Gong‐Bin Huang, Wei‐Hua Huang, Jing Guo, Dong‐Liang Xu, Xiao‐Chen Qu, Pei‐Hong Zhai, Xiu‐Hua Zheng, Jiang Weng and Gui Lu

Adv Synth Catal, 2019, 361, 1241
DOI: 10.1002/adsc.201801446

Time‐Economical Synthesis of Bis‐Spiro Cyclopropanes via Cascade 1,6‐Conjugate Addition/Dearomatization Reaction of para‐Quinone Methides with 3‐Chlorooxindoles

Jing‐Ru Zhang, Hai‐Shan Jin, Jin Sun, Jie Wang and Li‐Ming Zhao

Eur J Org Chem, 2020, 2020, 4988
DOI: 10.1002/ejoc.202000830

Direct Synthesis of Indolines via Cyclization of Tertiary Aryl Amines with Iodonium Ylides under Sole Visible Light Irradiation

Yan‐Rui Zhao, Lei Li and Jun Xuan

Adv Synth Catal, 2023, 365, 110
DOI: 10.1002/adsc.202201085

Bifunctional Phosphonium Salt Directed Enantioselective Formal [4 + 1] Annulation of Hydroxyl-Substituted para-Quinone Methides with α-Halogenated Ketones

Jian-Ping Tan, Peiyuan Yu, Jia-Hong Wu, Yuan Chen, Jianke Pan, Chunhui Jiang, Xiaoyu Ren, Hong-Su Zhang and Tianli Wang

Org. Lett., 2019, 21, 7298
DOI: 10.1021/acs.orglett.9b02560

An Access to Highly Functionalized Dihydrobenzofuran Spirooxindole Scaffolds

Daqian Wang, Jing Sun, Ying Han, Qiu Sun and Chao-Guo Yan

Org. Lett., 2022, 24, 7790
DOI: 10.1021/acs.orglett.2c03123

Synthesis of Functionalized Benzofurans from para-Quinone Methides via Phospha-1,6-Addition/O-Acylation/Wittig Pathway

Yan-Cheng Liou, Praneeth Karanam, Yeong-Jiunn Jang and Wenwei Lin

Org. Lett., 2019, 21, 8008
DOI: 10.1021/acs.orglett.9b03001

Synthesis of 1,4-Dihydroquinolines and 4H-Chromenes via Organocatalytic Domino Aza/Oxa-Michael/1,6-Addition Reactions of para-Quinone Methides and Ynals

Junwei Wang, Quanjin Rong, Lei Zhao, Xiang Pan, Lin Zhao, Kun Zhao and Lihong Hu

J. Org. Chem., 2020, 85, 11240
DOI: 10.1021/acs.joc.0c01315

Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents

Akira Yoshimura and Viktor V. Zhdankin

Chem. Rev., 2024, 124, 11108
DOI: 10.1021/acs.chemrev.4c00303

Highly Diastereoselective Synthesis of Tetrahydroquinoline Derivatives via [4 + 2] Annulation of Ortho-Tosylaminophenyl-Substituted Para-Quinone Methides and Cyanoalkenes

Taiwei Dong, Peifeng Wei, Min Li, Feng Gao and Yuan Qin

Front. Chem., 2021, 9
DOI: 10.3389/fchem.2021.764866

Base-Mediated Annulation of ortho-Iminophenols and ortho-Vinylphenols with MBH Carbonates of Isatins: Straightforward Access to Dihydrobenzofuran and Benzofuran Derivatives

Daqian Wang, Xing Liu, Jing Sun, Ying Han and Chao-Guo Yan

J. Org. Chem., 2024, 89, 15472
DOI: 10.1021/acs.joc.4c01501

Synthesis of para-Quinone Methides via Oxidative Ring-Opening of Spiro-cyclopropanyl-cyclohexadienones

Chaoxing Cui, Jianli Wu, Xixi Song and Miaomiao Li

Synthesis, 2022, 54, 4802
DOI: 10.1055/a-1878-8272

para‐Quinone Methides as Acceptors in 1,6‐Nucleophilic Conjugate Addition Reactions for the Synthesis of Structurally Diverse Molecules

Carolina G. S. Lima, Fernanda P. Pauli, Dora C. S. Costa, Acácio S. de Souza, Luana S. M. Forezi, Vitor F. Ferreira and Fernando de Carvalho da Silva

Eur J Org Chem, 2020, 2020, 2650
DOI: 10.1002/ejoc.201901796

Recyclable Bismuth Complex Catalyzed 1,6‐Conjugate Addition of Various Nucleophiles to para‐Quinone Methides: Expedient Access to Unsymmetrical Diaryl‐ and Triarylmethanes

Xianghao Liang, Haiyan Xu, Hanlin Li, Lizhuang Chen and Hongfei Lu

Eur J Org Chem, 2020, 2020, 217
DOI: 10.1002/ejoc.201901732

Base‐Mediated [4+1] Annulation Strategy for Modular Assembly of Alkynyl/Carboxylated Dihydrobenzofurans

Yangzilin Kong, Yinsong Wu, Yanan Liu, Binbin Fei, Mengdi Wu, Ni Gu, Qiang Tang and Xinwei He

Eur J Org Chem, 2025, 28
DOI: 10.1002/ejoc.202401455

C2-Arylated Indoles and Benzofurans through Formal (4 + 1) Annulation of N-Sulfonyl-2-aminobenzaldehydes and Salicylaldehyde Derivatives with Electron-Deficient Benzyl Chlorides

Lillian A. de Ceuninck van Capelle, Kimia Rahmannia, James M. Macdonald, Christopher Richardson, Michael G. Gardiner, John H. Ryan, Rasool Babaahmadi, Steven M. Wales and Christopher J. T. Hyland

J. Org. Chem., 2024, 89, 17488
DOI: 10.1021/acs.joc.4c02231

Iridium‐Catalyzed [4+3] Cyclization of ortho‐Tosylaminophenyl‐Substituted para‐Quinone Methides with Vinylic Oxiranes/Vinyl Aziridines

Junwei Wang, Lin Zhao, Caihong Li, Lei Zhao, Kun Zhao, Yang Hu and Lihong Hu

Asian J Org Chem, 2021, 10, 2152
DOI: 10.1002/ajoc.202100296

[4+2]‐Cycloaddition of para‐Quinone Methides with Hexahydro‐1,3,5‐Triazines: Access to 1,3‐Benzoxazine Derivatives

Xiao Cheng, Shuang‐Jing Zhou, Guo‐Yong Xu, Long Wang, Qing‐Qing Yang and Jun Xuan

Adv Synth Catal, 2020, 362, 523
DOI: 10.1002/adsc.201901169

Straightforward synthesis of novel spiroether derivatives

Olga V. Bobrovskaya, Aleksandr A. Russkih, Andrei N. Yankin, Maksim V. Dmitriev, Aleksandr S. Bunev and Vladimir L. Gein

Synthetic Communications, 2021, 51, 1731
DOI: 10.1080/00397911.2021.1903930

Curcumin as a Cinnamoyl Transfer Reagent via C–C(CO) Bond Scissoring in the Microwave-Assisted Reaction with Hydroxy-p-QMs

Deepak Kumar, Abhishek R. Tiwari and Irishi N. N. Namboothiri

J. Org. Chem., 2025, 90, 9757
DOI: 10.1021/acs.joc.5c00609

Ambiphilic p-Quinone Methides and α-Imino Ketones: Ca(II)-Catalyzed, One-Pot, Three-Component Synthesis of Benzoxazines

Srinivasarao Yaragorla and Doma Arun

J. Org. Chem., 2026, 91, 4740
DOI: 10.1021/acs.joc.5c03236

Enantioselective Catalytic [4+1]‐Cyclization of ortho‐Hydroxy‐para‐Quinone Methides with Allenoates

Katharina Zielke, Ondřej Kováč, Michael Winter, Jiří Pospíšil and Mario Waser

Chemistry A European J, 2019, 25, 8163
DOI: 10.1002/chem.201901784

Metal‐Free Regioselective 1,6‐Conjugate Addition of Sulfide to para‐Quinone Methides: Simple Access to E‐Selective Thiaoxacyclophanes

Sambasivarao Kotha, Naveen K. Gupta and Balaji U. Solanke

ChemistrySelect, 2023, 8
DOI: 10.1002/slct.202302672

Visible light and base promoted O-H insertion/cyclization of para-quinone methides with aryl diazoacetates: An approach to 2,3-dihydrobenzofuran derivatives

Shuangjing Zhou, Baogui Cai, Chuxia Hu, Xu Cheng, Lei Li and Jun Xuan

Chinese Chemical Letters, 2021, 32, 2577
DOI: 10.1016/j.cclet.2021.03.010

Addition of Sydnones to para‐Quinone Methides: Selective 1,6‐Additions and Oxidative C−H Functionalizations

Lavina Gladis Serrao, S. Naveenkumar and Mahagundappa R. Maddani

Eur J Org Chem, 2024, 27
DOI: 10.1002/ejoc.202400703

Recent advances in the cyclization of para-quinone methides

Xianping Liu, Yining Ren, Longzhi Zhu, Tao Li, Weifeng Xu, Yu Liu, Ke-Wen Tang and Biquan Xiong

Tetrahedron, 2023, 148, 133655
DOI: 10.1016/j.tet.2023.133655

A Facile Route to Pyrazolo[1,2‐a]cinnoline via Rhodium(III)‐catalyzed Annulation of Pyrazolidinoes and Iodonium Ylides

Zi Yang, Yi Zhou, Haigang Li, Jieni Lei, Pingping Bing, Binsheng He and Yaqian Li

Asian J Org Chem, 2022, 11
DOI: 10.1002/ajoc.202100656

Synthesis of 2,4‐Diaryl‐1,3‐benzoxazines via FeCl3‐Catalyzed Annulation of ortho‐Hydroxyphenyl‐Substituted para‐Quinone Methides with Imidates

Jing‐Ru Zhang, Hai‐Shan Jin, Ru‐Bing Wang and Li‐Ming Zhao

Adv Synth Catal, 2019, 361, 4811
DOI: 10.1002/adsc.201900842