Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis
DOI: 10.1055/a-2784-2363
DOI: 10.1055/a-2784-2363
Paper
A Practical Synthesis of 3-Ylidenephthalides by the Rh-Catalyzed Tandem Reactions of Benzoic acids and Alkynyl Chlorides
Authors

Abstract
A synthesis of 3-ylidenephthalides with high practicality and efficiency, using benzoic acids and alkynyl chlorides as substrate, was realized by the rhodium catalysis. The utilization of alkynyl chlorides enabled this reaction has advantages of broad substrates scope, mild reaction condition, high selectivity, and yields.
Publication History
Received: 12 November 2025
Accepted after revision: 08 January 2026
Accepted Manuscript online:
09 January 2026
Article published online:
26 January 2026
© 2026. Thieme. All rights reserved.
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
References
- 1a León A, Del-Ángel M, Ávila JL, Delgado G. Prog Chem Org Nat Prod 2017; 104: 127-246
- 1b Wei X, Zeng Y, Sun C, Meng F, Wang Y. Fitoterapia 2022; 160: 105223
- 2a Petrignet J, Thibonnet J, Commeiras L, Gueyrard G. Eur J Org Chem 2022; e202200344
- 2b Eddebbarh E, Moutardier L, Thibonnet J, Camiade E, Petrignet J. Eur J Org Chem 2024; 27: e202301303
- 2c Ballarín-Marión M, Herrera-Luna JC, Corcé V. et al. J Org Chem 2024; 89: 16242-16248
- 2d Wang X, Wang S, Zhang W, Han Y, Chen X, Li G. Green Synth Catal
- 2e Abhang RV, Bhagwata PN, Handore KL. Org Biomol Chem 2025; 23: 7702-7708
- 3 Rambabu D, Kumar GP, Kumar BD, Kapavarapu R, Rao MVB, Pal M. Tetrahedron Lett 2013; 54: 2989-2995
- 4a Kumar MR, Irudayanathan FM, Moon JH, Lee S. Adv Synth Catal 2013; 355: 3221-3230
- 4b Dhara S, Singha R, Ghosh M. et al. RSC Adv 2014; 4: 42604-42607
- 5 Petrignet J, Inack-Ngi S, Abarbri M, Thibonnet J. Tetrahedron Lett 2014; 55: 982-984
- 6 Kumar JS, Thirupataiah B, Medishetti R. et al. Eur J Med Chem 2020; 201: 112335
- 7 Fan F, Chen L, Wang G. Chin J Org Chem 2024; 44: 3467-3475
- 8a Chaudary S, Shyamlal BRK, Yadav L, Tiwari MK, Kumar K. RSC Adv 2018; 8: 23152-23162
- 8b Shyamlal BRK, Yadav L, Tiwari MK. et al. Sci Rep 2020; 10: 2307
- 9 He H-F, Wang Y, Zou C, Tu Z, Xu Y, Yin J. ACS Omega 2022; 7: 3060-3063
- 10 Mei R, Zhang S-K, Ackermann L. Org Lett 2017; 19: 3171-3174
- 11 Shi S, Chen C-H, Chai Y. et al. J Org Chem 2019; 84: 9161-9168
- 12 Liu Y, Yang Y, Wang X, Zhang L, Cheng Y, You J. Organometallics 2016; 35: 1350-1353
- 13 Han W-J, Pu F, Fan J, Liu Z-W, Shi X-Y. Adv Synth Catal 2017; 359: 3520-3525
- 14 Nandi D, Ghosh D, Chen S-J, Kuo B-C, Wang NM, Lee HM. J Org Chem 2013; 78: 3445-3451
- 15 Jambu S, Tamizmani M, Jeganmohan M. Org Lett 2018; 20: 1982-1986
- 16 Zhao X, Gao Z, Luo Y. Org Lett 2024; 26: 9717-9721
- 17 In Ref. 11, 1,4-dicarboxylic acid was tried and no desired product obtained
- 18a Ye B, Cramer N. Acc Chem Res 2015; 48: 1308-1318
- 18b Hummel JR, Boerth JA, Ellman JA. Chem Rev 2017; 117: 9163-9227
- 18c Qi X, Li Y, Bai R, Lan Y. Acc Chem Res 2017; 50: 2799-2808
- 18d Wang R, Xie X, Liu H, Zhou Y. Catalysts 2019; 9: 823-851
- 18e Mas-Roselló J, Herraiz AG, Audic B, Laverny A, Cramer N. Angew Chem Int Ed 2021; 60: 13198-13224
- 19 Zhao X, Fan C, He J, Luo Y. Org Lett 2022; 24: 9169-9173
- 20 He J, Zhang J, Li X, Shi H, Du Y. Chem Commun 2022; 58: 9096-9099
- 21 Yuan Q, Chen ZB, Zhang FL, Zhu YM. Org Biomol Chem 2017; 15: 1628-1635
For earlier miscellaneous synthetic protocol see the review and the literature cited within:
For recent advances see:
For selected reviews of Rh(III)-catalyzed C–H activations, see: