研究论文
杨帆a,☘, 范小梦a,☘, 姚雪婧b, 米瑞杰b,*, 于松杰b,*, 李兴伟b,*, 肖建a,*
收稿日期:
2024-05-10
修回日期:
2024-06-16
Fan Yanga,☘, Xiaomeng Fana,☘, Xuejing Yaob, Ruijie Mib,*, Songjie Yub, Xingwei Lib,*, Jian Xiaoa,*
Received:
2024-05-10
Revised:
2024-06-16
Contact:
*E-mail: About author:
☘These authors contribute equally to this work.
Supported by:
文章分享
本工作报道了氧化还原中性条件下过渡金属铑催化氧化锍叶立德C-H 键活化与两类环状重氮化合物发生环化反应,分别合成了结构多样性的稠环和螺环。该反应通过螯合辅助的C-H活化、卡宾插入以及随后的分子内[3+3]环化或者[4+1]螺环化反应进行。
杨帆, 范小梦, 姚雪婧, 米瑞杰, 于松杰, 李兴伟, 肖建. 铑(III)催化氧化锍叶立德和重氮化合物环化偶联反应[J]. 有机化学, doi: 10.6023/cjoc202405011.
Fan Yang, Xiaomeng Fan, Xuejing Yao, Ruijie Mi, Songjie Yu, Xingwei Li, Jian Xiao. Rhodium(III)-Catalyzed Annulative Coupling between Sulfoxonium Ylides and Diazo Compounds via C-H Activation[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202405011.
[1] For selected reviews, see: (a) Gutekunst, W. R.; Baran, P. S. C-H Functionalization Logic in Total Synthesis. Chem. Soc. Rev. 2011, 40, 1976-1991. (b) Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Recent Advances in the Transition Metal-Catalyzed twofold Oxidative C-H Bond Activation Strategy for C-C and C-N Bond Formation. Chem. Soc. Rev. 2011, 40, 5068-5083. (c) Ackermann, L. Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope. Chem. Rev. 2011, 111, 1315-1345. (d) He, J.; Wasa, M.; Chan, K. S. L.; Shao, Q.; Yu, J. Q. Palladium-Catalyzed Transformations of Alkyl C-H Bonds. Chem. Rev. 2017, 117, 8754-8786. (e) Yang, Y. D.; Lan, J. B.; You, J. S.Oxidative C-H/C-H Coupling Reactions between Two (Hetero) Arenes. Chem. Rev. 2017, 117, 8787-8863. (f) Dong, Z.; Ren, Z.; Thompson, S. J.; Xu, Y.; Dong, G. B. Transition-Metal-Catalyzed C-H Alkylation Using Alkenes. Chem. Rev. 2017, 117, 9333-9403. (g) Hummel, J. R.; Boerth, J. A.; Ellman, J. A. Transition-Metal-Catalyzed C-H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds. Chem. Rev. 2017, 117, 9163-9227. (h) Gandeepan, P.; Müller, T.; Zell, D.; Cera, G.; Warratz, S.; Ackermann, L. 3d Transition Metals for C-H Activation. Chem. Rev. 2019, 119, 2192-2452. (i) Yu, X.; Zhang, Z.; Niu, J. L.; Shi, B. F. Coordination-Assisted, Transition-Metal-Catalyzed Enantioselective Desymmetric C-H Functionalization. Org. Chem. Front. 2022, 9, 1458-1484. (j) Lu, M. Z.; Goh, J.; Maraswami, M.; Jia, Z.; Tian, J. S.; Loh, T. P. Recent Advances in Alkenyl sp2 C-H and C-F Bond Functionalizations: Scope, Mechanism, and Applications. Chem. Rev. 2022, 122, 17479-17646. (k) Brandes, D. S.; Ellman, J. A. C-H Bond Activation and Sequential Addition to Two Different Coupling Partners: A Versatile Approach to Molecular Complexity. Chem. Soc. Rev. 2022, 51, 6738-6756. (l) Yu, I. F.; Wilson, J. W.; Hartwig, J. F. Transition-Metal-Catalyzed Silylation and Borylation of C-H Bonds for the Synthesis and Functionalization of Complex Molecules. Chem. Rev. 2023, 123, 11619-11663. [2] (a) Ritleng, V.; Sirlin, C.; Pfeffer, M. Ru-, Rh-, and Pd-Catalyzed C-C Bond Formation Involving C-H Activation and Addition on Unsaturated Substrates: Reactions and Mechanistic Aspects. Chem. Rev. 2002, 102, 1731-1770. (b) Colby, D. A.; Bergman, R. G.; Ellman, J. A. Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation. Chem. Rev. 2010, 110, 624-655. (c) Shi, Z. Z.; Koester, D. C.; Boultadakis-Arapinis, M.; Glorius, F. Rh(III)-Catalyzed Synthesis of Multisubstituted Isoquinoline and Pyridine N-Oxides from Oximes and Diazo Compounds. J. Am. Chem. Soc. 2013, 135, 12204-12207. (d) Piou, T.; Rovis, T. Electronic and Steric Tuning of a Prototypical Piano Stool Complex: Rh(III) Catalysis for C-H Functionalization. Acc. Chem. Res. 2018, 51, 170-180. (e) Zeng, Z. Y.; Gao, H.; Zhou, Z.; Yi, W. Intermolecular Redox-Neutral Carboamination of C-C Multiple Bonds Initiated by Transition-Metal-Catalyzed C-H Activation. ACS Catal. 2022, 12, 14754-14772. (f) Liu, C. X.; Yin, S. Y.; Zhao, F.; Yang, H.; Feng, Z.; Gu, Q.; You, S. L. Rhodium-Catalyzed Asymmetric C-H Functionalization Reactions. Chem. Rev. 2023, 123, 10079-10134. [3] (a) Li, A. H.; Dai, L. X.; Aggarwal, V. K. Asymmetric Ylide Reac tions: Epoxidation, Cyclopropanation, Aziridination, Olefination, and Rearrangement. Chem. Rev. 1997, 97, 2341-2372. (b) Aggarwal, V. K.; Winn, C. L. Catalytic, Asymmetric Sulfur Ylide-Mediated Epoxidation of Carbonyl Compounds: Scope, Selectivity, and Applications in Synthesis. Acc. Chem. Res. 2004, 37, 611-620. (c) Lu, L. Q.; Li, T; Wang, Q.; Xiao, W. Beyond Sulfide-Centric Catalysis: Recent Advances in the Catalytic Cyclization Reactions of Sulfur Ylides. Chem. Soc. Rev. 2017, 46, 4135-4149. [4] (a) Kumar, A.; Sherikar, M. S.; Hanchate, V.; Prabhu, K. R. Applica tion of Sulfoxonium Ylide in Transition-Metal-Catalyzed C-H Bond Activation and Functionalization Reactions. Tetrahedron 2021, 101, 132478-132511. (b) Bhorali, P.; Sultana, S.; Gogoi, S. Recent Advances in Metal-Catalyzed C-H Bond Functionalization Reactions of Sulfoxonium Ylides. Asian J. Org. Chem. 2022, 11, e202100754. (c) Singh, A.; Kumar, S.; Volla, C. M. R. α-Carbonyl Sulfoxonium Ylides in Transition Metalcatalyzed C-H Activation: a Safe Carbene Precursor and a Weak Directing Group. Org. Biomol. Chem. 2023, 21, 879-909. [5] (a) Barday, M.; Janot, C.; Halcovitch, N. R.; Muir, J.; Aïssa, C. Cross-Coupling of α-Carbonyl Sulfoxonium Ylides with C-H Bonds. Angew. Chem., Int. Ed. 2017, 56, 13117-13121. (b) Xu, Y. W.; Zhou, X. K.; Zheng, G. F.; Li, X. W. Sulfoxonium Ylides as a Carbene Precursor in Rh(III)-Catalyzed C-H Acylmethylation of Arenes. Org. Lett. 2017, 19, 5256-5259. [6] (a) Xu, Y. W.; Yang, X. F.; Zhou, X. K.; Kong, L. H.; Li, X. W. Rhodium(III)-Catalyzed Synthesis of Naphthols via C-H Activation of Sulfoxonium Ylides. Org. Lett. 2017, 19, 4307-4310. (b) Yu, Y. Q.; Wu, Q. L.; Liu, D.; Yu, L.; Tan, Z.; Zhu, G. G. Synthesis of 1-naphthols via Cp*Co(iii)-Catalyzed C-H Activation and Cyclization of Sulfoxonium Ylides with Alkynes. Org. Chem. Front. 2019, 6, 3868-3873. (c) Hanchate, V.; Kumar, A.; Prabhu, K. R. Synthesis of Naphthols by Rh(III)-Catalyzed Domino C-H Activation, Annulation, and Lactonization Using Sulfoxonium Ylide as a Traceless Directing Group. Org. Lett. 2019, 21, 8424-8428. (d) Xie, W.; Lin, B.; Jian, X.; Lin, Q. and Shi, J. Synlett, 2020, 1482-1486. (e) Liu, R. X.; Wei, Y.; Shi, M. Rhodium(III)-Catalyzed Cross Coupling of Sulfoxonium Ylides and 1,3-Diynes to Produce Naphthol-Indole Derivatives: An Arene ortho C-H Activation/Annulation Cascade. ChemCatChem. 2020, 12, 5903-5906. (f) Xie, W. C.; Jian, X. Y.; Zhang, L. Y.; Jin, K. X.; Shi, J. J.; Zhu, F. Synthesis of C3-Sulfone Substituted Naphthols via Rhodium(iii)-Catalyzed Annulation of Sulfoxonium Ylides with Alkynylsulfones. Org. Biomol. Chem. 2021, 19, 1498-1502. (g) Wang, P. Y.; Huang, Y. L.; Jing, J. R.; Wang, F.; Li, X. W. Rhodium(III)-Catalyzed Atroposelective Synthesis of C-N Axially Chiral Naphthylamines and Variants via C-H Activation. Org. Lett. 2022, 24, 2531-2535. [7] (a) Wang, P. Y.; Xu, Y. W.; Sun, J. Q.; Li, X. W. Rhodium(III)-Catalyzed Chemo-Divergent Couplings of Sulfoxonium Ylides with Oxa/Azabicyclic Olefins. Org. Lett. 2019, 21, 8459-8463. (b) Lou, J.; Wang, Q. N.; Zhou, Y.-G.; Yu, Z. K. Rhodium(III)-Catalyzed Annulative Coupling of Sulfoxonium Ylides and Allenoates: An Arene C-H Activation/Cyclopropanation Cascade. Org. Lett. 2019, 21, 9217-9222. [8] (a) Kommagalla, Y.; Ando, S.; Chatani, N. Rh(III)-Catalyzed Reac tion of α-Carbonyl Sulfoxonium Ylides and Alkenes: Synthesis of Indanones via [4 + 1] Cycloaddition. Org. Lett. 2020, 22, 1375-1379. (b) Hanchate, V.; Devarajappa, R.; Prabhu, K. R. Sulfoxonium-Ylide-Directed C-H Activation and Tandem (4 + 1) Annulation. Org. Lett. 2020, 22, 2878-2882. [9] Dong Y.; Yu J.-T.; Sun S.; Cheng J.Rh(iii)-Catalyzed Sequential ortho-C-H Oxidative Arylation/Cyclization of Sulfoxonium Ylides with Quinones Toward 2-hydroxy-dibenzo[b, d]pyran-6-ones. Chem. Commun. 2020, 56, 6688-6691. [10] (a) Yu, Y. Q.; Xia, Z.; Wu, Q. L.; Liu, D.; Yu, L.; Xiao, Y. J.; Tan, Z.; Deng, W.; Zhu, G. G. Direct synthesis of benzoxazinones via Cp*Co(III)-catalyzed C-H Activation and Annulation of Sulfoxonium Ylides with Dioxazolones. Chin. Chem. Lett. 2021, 32, 1263-1266. (b) Yin, C. L.; Li, L. H.; Yu, C. M. Rh(iii)-catalyzed C-H Annulation of Sulfoxonium Ylides with Iodonium Ylides towards Isocoumarins. Org. Biomol. Chem. 2022, 20, 1112-1116. [11] For representative individual reports, see: (a) Chan, W.-W.; Lo, S.-F.; Zhou, Z. Y.; Yu, W.-Y. Rh-Catalyzed Intermolecular Carbenoid Functionalization of Aromatic C-H Bonds by α-Diazomalonates. J. Am. Chem. Soc. 2012, 134, 13565-13568. (b) Yu, X. Z.; Yu, S. J.; Xiao, J.; Wan, B. S.; Li, X. W. Rhodium(III)-Catalyzed Azacycle-Directed Intermolecular Insertion of Arene C-H Bonds into α-Diazocarbonyl Compounds. J. Org. Chem. 2013, 78, 5444-5452. (c) Hu, F. D.; Xia, Y.; Ye, F.; Liu, Z. X.; Ma, C.; Zhang, Y.; Wang, J. Rhodium(III)-Catalyzed ortho Alkenylation of N-Phenoxyacetamides with N-Tosylhydrazones or Diazoesters through C-H Activation. Angew. Chem., Int. Ed. 2014, 53, 1364-1367. (d) Liang, Y. J.; Yu, K.; Li, B.; Xu, S. S.; Song, H. B.; Wang, B. Q. Rh(iii)-catalyzed Synthesis of 1-aminoindole Derivatives from 2-acetyl-1-Arylhydrazines and Diazo Compounds in Water. Chem. Commun. 2014, 50, 6130-6133. (e) Ford, A.; Miel, H.; Ring, A.; Slattery, C. N.; Maguire, A. R.; McKervey, M. A. Modern Organic Synthesis with α-Diazocarbonyl Compounds. Chem. Rev. 2015, 115, 9981-10080. (f) Yu, S. J.; Liu, S.; Lan, Y.; Wan, B. S.; Li, X. W. Rhodium-Catalyzed C-H Activation of Phenacyl Ammonium Salts Assisted by an Oxidizing C-N Bond: A Combination of Experimental and Theoretical Studies. J. Am. Chem. Soc. 2015, 137, 1623-1631. (g) Wu, J. Q.; Yang, Z.; Zhang, S.-S.; Jiang, C. Y.; Li, Q.; Huang, Z. S.; Wang, H. From Indoles to Carbazoles: Tandem Cp*Rh(III)-Catalyzed C-H Activation/Brønsted Acid-Catalyzed Cyclization Reactions. ACS Catal. 2015, 5, 6453-6457. (h) Yang, Y.; Wang, X.; Li, Y. C.; Zhou, B. A [4+1] Cyclative Capture Approach to 3H-Indole-N-oxides at Room Temperature by Rhodium(III)-Catalyzed C-H Activation. Angew. Chem., Int. Ed. 2015, 54, 15400-15404. (i) Dateer, R. B.; Chang, S. Rh(III)-Catalyzed C-H Cyclization of Arylnitrones with Diazo Compounds: Access to N-Hydroxyindolines. Org. Lett. 2016, 18, 68-71. (j) Li, J.; Tang, M. Y.; Zang, L.; Zhang,X. L.; Zhang,Z.; Ackermann,L. Amidines for Versatile Cobalt(III)-Catalyzed Synthesis of Isoquinolines through C-H Functionalization with Diazo Compounds. Org. Lett. 2016, 18, 2742-2745. For selected reviews, see:(k) Xia, Y.; Qiu, D.; Wang, J. B. Transition-Metal-Catalyzed Cross-Couplings through Carbene Migratory Insertion. Chem. Rev. 2017, 117, 13810-13889. (l) Wang, M. M.; Kong, L. H.; Wu,Q. Y.; Li, X. W. Ruthenium- and Rhodium-Catalyzed Chemodivergent Couplings of Ketene Dithioacetals and α-Diazo Ketones via C-H Activation/Functionalization. Org. Lett. 2018, 20, 4597-4600. (m) Xiang, Y. Y.; Wang C.; Ding, Q. P.; Peng, Y. Y. Diazo Compounds: Versatile Synthons for the Synthesis of Nitrogen Heterocycles via Transition Metal-Catalyzed Cascade C-H Activation/Carbene Insertion/Annulation Reactions. Adv. Synth. Catal. 2019, 361, 919-944. (n) He, Y.; Huang, Z. L.; Wu, K. K.; Ma, J.; Zhou, Y.-G.; Yu, Z. K. Recent Advances in Transition-Metal-Catalyzed Carbene Insertion to C-H Bonds. Chem. Soc. Rev. 2022, 51, 2759-2852. [12] (a) Zhang, S. S.; Jiang, C. Y.; Wu, J. Q.; Liu, X. G.; Li, Q.; Huang, Z. S.; Li, D.; Wang, H. Cp*Rh(iii) and Cp*Ir(iii)-Catalysed Redox-neutral C-H Arylation with Quinone Diazides: Quick and Facile Synthesis of Arylated Phenols. Chem. Commun. 2015, 51, 10240-10243. (b) Jia, Z. J.; Merten, C.; Gontla, R.; Daniliuc, C. G.; Antonchick, A. P.; Waldmann, H. General Enantioselective C-H Activation with Efficiently Tunable Cyclopentadienyl Ligands. Angew. Chem., Int. Ed. 2017, 56, 2429-2434. (c) Jang, Y. S.; Wozniak, L.; Pedroni, J.; Cramer, N. Access to P- and Axially Chiral Biaryl Phosphine Oxides by Enantioselective CpXIrIII- Catalyzed C-H Arylations. Angew. Chem., Int. Ed. 2018, 57, 12901-12905. (d) Zou, Y.; Wang, P. Y.; Kong, L. H.; Li, X. W. Rhodium-Catalyzed Atroposelective C-H Arylation of (Hetero) Arenes Using Carbene Precursors as Arylating Reagents. Org. Lett. 2022, 24, 3189-3193. [13] (a) Han, X.; Kong, L. H.; Feng, J. M.; Li, X. W. Rhodium(III)-catalyzed Syn thesis of Spirocyclic Isoindole N-oxides and IsoBenzofuranones via C-H Activation and Spiroannulation. Chem. Commun. 2020, 56, 5528-5531. (b) Kong, L. H.; Han, X.; Liu, S.; Zou, Y.; Lan, Y.; Li, X. W. Rhodium(III)-Catalyzed Asymmetric Access to Spirocycles through C-H Activation and Axial-to-Central Chirality Transfer. Angew. Chem., Int. Ed. 2020, 59, 7188-7192. [14] Chen R. J.; Cui S. L.Rh(III)-Catalyzed C-H Activation/Cyclization of Benzamides and Diazonaphthalen-2(1H)-ones for Synthesis of Lactones. Org. Lett. 2017, 19, 4002-4005. [15] Giri C. K.; Mondal S.; Baidya M. Ruthenium(II)-catalyzed C-H activation/lactonization of Aromatic Acids with Diazonaphthoquinones: Regioselective Synthesis of Polycyclic Coumarin Frameworks. Org. Chem. Front. 2023, 10, 5856-5862. [16] (a) Chen, X.; Wang, M. H.; Zhang, X. Y.; Fan, X. S. Rh(III)-Catalyzed Cas cade Reactions of Sulfoxonium Ylides with α‑Diazocarbonyl Compounds: An Access to Highly Functionalized Naphthalenones. Org. Lett. 2019, 21, 2541-2545. (b) Song, X. H.; Han, X.; Zhang, R.; Liu, H.; Wang, J. Rhodium(III)-Catalyzed [4+2] Annulation via C-H Activation: Synthesis of Multi-Substituted Naphthalenone Sulfoxonium Ylides. Molecules 2019, 24, 1884-1901. [17] Xu Y. W.; Yang X. F.; Zhou X. K.; Kong L. H.; Li X. W.Rhodium(III)-Catalyzed Synthesis of Naphthols via C-H Activation of Sulfoxonium Ylides. Org. Lett. 2017, 19, 4307-4310. [18] Zou Y.; Wang P. Y.; Kong L. H.; Li X. W.Rhodium-Catalyzed Atroposelective C-H Arylation of (Hetero) Arenes Using Carbene Precursors as Arylating Reagents. Org. Lett. 2022, 24, 3189-3193. [19] Sun L. C.; Liu B. X.; Zhao Y. L.; Chang J. B.; Kong L. H.;Fen Wang, F.; Deng, W. Q.; Li, X. W.Rhodium(iii)-catalyzed asymmetric [4+1] spiroannulations of O-pivaloyl oximes with α-diazo compounds. Chem. Commun. 2021, 57, 8268-8271. |
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