Communication
ChemComm
Notes and references
1 (a) D. A. Colby, R. G. Bergman and J. A. Ellman, Chem. Rev., 2010,
110, 624–655; (b) T. Piou and T. Rovis, Acc. Chem. Res., 2018, 51,
170–180; (c) S. Rej and N. Chatani, Angew. Chem., Int. Ed., 2019, 58,
8304–8329; (d) G. Song and X. Li, Acc. Chem. Res., 2015, 48,
1007–1020; (e) G. Song, F. Wang and X. Li, Chem. Soc. Rev., 2012,
41, 3651–3678; ( f ) B. Ye and N. Cramer, Acc. Chem. Res., 2015, 48,
1308–1318.
2 (a) P. H. Chen, B. A. Billett, T. Tsukamoto and G. Dong, ACS Catal.,
2017, 7, 1340–1360; (b) G. Fumagalli, S. Stanton and J. F. Bower,
Chem. Rev., 2017, 117, 9404–9432; (c) M. Murakami and N. Ishida,
J. Am. Chem. Soc., 2016, 138, 13759–13769; (d) L. Souillart and
N. Cramer, Chem. Rev., 2015, 115, 9410–9464.
3 (a) H.-M. Chen, G. Liao, C.-K. Xu, Q.-J. Yao, S. Zhang and B.-F. Shi,
CCS Chem., 2021, 3, 455–465; (b) Q. Li, X. Yuan, B. Li and B. Wang,
Chem. Commun., 2020, 56, 1835–1838; (c) X. Zhou, S. Yu, L. Kong and
X. Li, ACS Catal., 2016, 6, 647–651; (d) Z. Nairoukh, M. Cormier and
I. Marek, Nat. Rev. Chem., 2017, 1, 0035.
4 A. Nikolaev and A. Orellana, Synthesis, 2016, 1741–1768.
5 B. Q. Cheng, S. X. Zhang, Y. Y. Cui, X. Q. Chu, W. Rao, H. Xu,
G. Z. Han and Z. L. Shen, Org. Lett., 2020, 22, 5456–5461.
6 (a) L. Chen, H. Quan, Z. Xu, H. Wang, Y. Xia, L. Lou and W. Yang,
Nat. Commun., 2020, 11, 2151; (b) J. Hao, X. Guo, S. He, Z. Xu,
L. Chen, Z. Li, B. Song, J. Zuo, Z. Lin and W. Yang, Nat. Commun.,
2021, 12, 1304; (c) B. Song, P. Xie, Y. Li, J. Hao, L. Wang, X. Chen,
Z. Xu, H. Quan, L. Lou, Y. Xia, K. N. Houk and W. Yang, J. Am. Chem.
Soc., 2020, 142, 9982–9992; (d) Y. Xu, L. Chen, Y. W. Yang, Z. Zhang
and W. Yang, Org. Lett., 2019, 21, 6674–6678.
7 (a) A. Awasthi, M. Singh, G. Rathee and R. Chandra, RSC. Adv., 2020,
10, 12626–12652; (b) R. Karmakar, P. Pahari and D. Mal, Chem. Rev.,
2014, 114, 6213–6284; (c) A. Renzetti and K. Fukumoto, Molecules,
2019, 24, 824.
8 (a) J. J. Beck and S. C. Chou, J. Nat. Prod., 2007, 70, 891–900;
(b) N. Zheng, F. Yao, X. Liang, Q. Liu, W. Xu, Y. Liang, X. Liu, J. Li
and R. Yang, Nat. Prod. Res., 2018, 32, 755–760; (c) J. Zou,
G. D. Chen, H. Zhao, Y. Huang, X. Luo, W. Xu, R. R. He, D. Hu,
X. S. Yao and H. Gao, Org. Lett., 2018, 20, 884–887.
9 (a) S. Cui, Y. Zhang and Q. Wu, Chem. Sci., 2013, 4, 3421–3426;
(b) J. Kim, S. W. Park, M. H. Baik and S. Chang, J. Am. Chem. Soc.,
2015, 137, 13448–13451; (c) B. V. Pati, A. Ghosh and P. C. Ravikumar,
Org. Lett., 2020, 22, 2854–2860.
10 The CCDC number of 3aa is 2058379 and more details can be
obtained from Cambridge Crystallographic Data Center†.
11 (a) M. Bissaro, M. Sturlese and S. Moro, Drug Discovery Today, 2020,
25, 1693–1701; (b) B. Diethelm-Varela, ChemMedChem, 2021, 16,
725–742; (c) A. Kashyap, P. K. Singh and O. Silakari, Curr. Top. Med.
Chem., 2018, 18, 2284–2293; (d) V. V. Kleandrova and A. Speck-
Planche, Mini-Rev. Med. Chem., 2020, 20, 1357–1374; (e) J. Osborne,
S. Panova, M. Rapti, T. Urushima and H. Jhoti, Biochem. Soc. Trans.,
2020, 48, 271–280; ( f ) L. Shi and N. Zhang, Molecules, 2021, 26,
576.
Fig. 3 Proposed mechanism.
insertion might take place to provide intermediate E. Finally, b-
H elimination could occur instead of protonation to give the
intermediate G, followed by Michael addition to afford desired
product 3aa with Rh (I), which was oxidized by Ag(I) and
reformed the active catalyst [Cp*Rh(OAc)2] for the next cycle.
In summary, we have developed a general and efficient
method to synthesize 3-substituted phthalides and a,b-
butenolides via Rh(III)-catalyzed cascade C–H activation/ring
opening C–C cleavage/cyclization of carboxylic acids with cyclo-
propanols. The reaction is characterized by a broad substrate
scope, excellent functional group tolerance, and mild condi-
tions. Moreover, this catalytic methodology has been success-
fully applied to late-stage functionalization of bioactive
compounds by the introduction of 3-substituted phthalides.
We gratefully acknowledge the 100 talent program of Chinese
Academy of Sciences, NSFC (21702217), ‘‘1000-Youth Talents
Plan’’, Shanghai-Youth Talent, National Science & Technology
Major Project‘‘ Key New Drug Creation and Manufacturing Pro-
gram’’ China (Number: 2018ZX09711002-006), Science and Tech-
nology Commission of Shanghai Municipality (18431907100) and
Shanghai-Technology Innovation Action Plan (18JC1415300).
12 (a) J. Li, Y. Zheng, M. Huang and W. Li, Org. Lett., 2020, 22,
5020–5024; (b) L. R. Mills, C. Zhou, E. Fung and
S. A. L. Rousseaux, Org. Lett., 2019, 21, 8805–8809; (c) Y. H. Zhang,
W. W. Zhang, Z. Y. Zhang, K. Zhao and T. P. Loh, Org. Lett., 2019, 21,
5101–5105.
Conflicts of interest
There are no conflicts to declare.
5932 | Chem. Commun., 2021, 57, 5929–5932
This journal is © The Royal Society of Chemistry 2021