Rh(I)-catalyzed enantioselective (3 + 2) transannulations of 1,2,3-thiadiazoles with P-chiral monodentate phosphines

References

• Kurandina, D.; Gevorgyan, V. Rhodium Thiavinyl Carbenes from 1,2,3-Thiadiazoles Enable Modular Synthesis of Multisubstituted Thiophenes. Org. Lett. 2016, 18, 1804–1807. DOI: 10.1021/acs.orglett.6b00541.
   PubMed Web of Science ®Google Scholar
• Son, J. Y.; Kim, J.; Han, S. H.; Kim, S. H.; Lee, P. H. Regioselective Synthesis of Dihydrothiophenes and Thiophenes via the Rhodium-Catalyzed Transannulation of 1,2,3-Thiadiazoles with Alkenes. Org. Lett. 2016, 18, 5408–5411. DOI: 10.1021/acs.orglett.6b02805.
   PubMed Web of Science ®Google Scholar
• Seo, B.; Kim, Y. G.; Lee, P. H. Synthesis of Isothiazole via the Rhodium-Catalyzed Transannulation of 1,2,3-Thiadiazoles with Nitriles. Org. Lett. 2016, 18, 5050–5053. DOI: 10.1021/acs.orglett.6b02499.
   PubMed Web of Science ®Google Scholar
• Seo, B.; Kim, H.; Kim, Y. G.; Baek, Y.; Um, K.; Lee, P. H. Synthesis of Bicyclic Isothiazoles through an Intramolecular Rhodium-Catalyzed Transannulation of Cyanothiadiazoles. J. Org. Chem. 2017, 82, 10574–10582. DOI: 10.1021/acs.joc.7b02077.
   PubMed Web of Science ®Google Scholar
• Kim, J. E.; Lee, J.; Yun, H.; Baek, Y.; Lee, P. H. Rhodium-Catalyzed Intramolecular Transannulation Reaction of Alkynyl Thiadiazole Enabled 5,n-Fused Thiophenes. J. Org. Chem. 2017, 82, 1437–1447. DOI: 10.1021/acs.joc.6b02614.
   PubMed Web of Science ®Google Scholar
• Liang, W.; Nakajima, K.; Nishibayashi, Y. Rhodium-Catalyzed Cyclization Reactions of Thiadiazoles with Phosphaalkynes to Prepare 1,3-Thiaphospholes. Eur. J. Org. Chem. 2020, 2020, 3879–3882. DOI: 10.1002/ejoc.202000506.
   Web of Science ®Google Scholar
• Zhou, B.; Wu, Q.; Dong, Z.; Xu, J. X.; Yang, Z. Rhodium-Catalyzed 1,1-Hydroacylation of Thioacyl Carbenes with Alkynyl Aldehydes and Subsequent Cyclization. Org. Lett. 2019, 21, 3594–3599. DOI: 10.1021/acs.orglett.9b01003.
   PubMed Web of Science ®Google Scholar
• Wu, Q.; Dong, Z.; Xu, J.; Yang, Z. Sulfur-Controlled and Rhodium-Catalyzed Formal (3 + 3) Transannulation of Thioacyl Carbenes with Alk-2-Enals and Mechanistic Insights. Org. Biomol. Chem. 2021, 19, 3173–3180. DOI: 10.1039/d1ob00116g.
   PubMed Web of Science ®Google Scholar
• Dong, Z.; Chen, C.; Wang, J.; Xu, J.; Yang, Z. Dual Roles of Bisphosphines and Epoxides: Rh-Catalyzed Highly Chemoselective and Diastereoselective (3 + 2) Transannulations of 1,2,3-Thiadiazoles with Cyanoepoxides. Org. Chem. Front. 2021, 8, 6687–6698. DOI: 10.1039/D1QO01220G.
   Web of Science ®Google Scholar
• Dong, Z.; Ma, M.; Xu, J.; Yang, Z. Catalytic (3 + 2) Umpolung Annulations of Alpha-Thioacyl Carbenes with Aryl Isothiocyanates. Chem. Commun. (Camb) 2022, 58, 7980–7983. DOI: 10.1039/d2cc90292c.
   PubMed Web of Science ®Google Scholar
• Chen, C.; Fang, S.; Dong, Z.; Xu, J.; Yang, Z. Catalytic Diastereospecific and Enantioselective (3 + 2) Transannulations of 1,2,3-Thiadiazoles with Strained Norbornene Derivatives. Org. Lett. 2022, 24, 2110–2114. DOI: 10.1021/acs.orglett.2c00330.
   PubMed Web of Science ®Google Scholar
• Chen, C.; Fang, S.; Yu, M.; Xu, J.; Yang, Z. Catalytic Site-Specific and Regioselective (3 + 2) Transannulations between 1,2,3-Thiadiazoles and Allenoates. Org. Chem. Front. 2023, 10, 661–667. DOI: 10.1039/D2QO01662A.
   Web of Science ®Google Scholar
• Wu, Q.; Chen, N.; Xu, J. Chemoselectivity in the Transannulation of 1,2,3-Thiadiazoles and Alk-2-Enenitriles: Specific Synthesis of 3-(Alk-1-Enyl)Isothiazoles. ChemistrySelect 2022, 7, e202103943. DOI: 10.1002/slct.202103943.
   Web of Science ®Google Scholar
• Lv, K.; Bao, X. Mechanistic Insights into the Rh(i)-Catalyzed Transan.ulation of 1,2,3-Thiadiazoles with Alkenes, Alkynes, and Nitriles: Does the Intermediacy of α-Thiavinyl Rh-Carbenoids Play an Important Role? Org. Chem. Front. 2021, 8, 310–318. DOI: 10.1039/D0QO01246G.
   Web of Science ®Google Scholar
• Marina, A. T.; Pernik, I.; Lewis, W.; Messerle, B. A.; Glukhareva, T. V.; Keaveney, S. T. Rh (I)-Catalyzed Denitrogenative Transformations of 1, 2, 3-Thiadiazoles: Ligand-Controlled Product Selectivity and the Structure of the Key Organorhodium Intermediate Revealed. ACS Catal. 2022, 12, 5574–5584. DOI: 10.1021/acscatal.2c01175.
   Web of Science ®Google Scholar
• Marina, A. T.; Pernik, I.; Lewis, W.; Messerle, B. A.; Glukhareva, T. V.; Keaveney, S. T. The Effect of the C5-Substituent on Regioselectivity in the Rh(I)-Catalyzed Intermolecular Transannulation of 1, 2, 3-Thiadiazoles with Phenylacetylene. Catal. Sci. Technol. 2023, 13, 2772–2782. DOI: 10.1039/D3CY00290J.
   Web of Science ®Google Scholar
• Wu, T.; Xu, G.; Tang, W. P-Chiral Phosphorus Ligands for Cross-Coupling and Asymmetric Hydrogenation Reactions. Aldrichimica Acta 2020, 53, 27–35.
   Web of Science ®Google Scholar
• Xu, G.; Senanayake, C. H.; Tang, W. P-Chiral Phosphorus Ligands Based on a 2,3-Dihydrobenzo [d] [1,3] Oxaphosphole Motif for Asymmetric Catalysis. Acc. Chem. Res. 2019, 52, 1101–1112. DOI: 10.1021/acs.accounts.9b00029.
   PubMed Web of Science ®Google Scholar
• Yang, H.; Tang, W. Efficient Enantioselective Syntheses of Chiral Natural Products Cacilitated by Ligand Design. Chem. Rec. 2020, 20, 23–40. DOI: 10.1002/tcr.201900003.
   PubMed Web of Science ®Google Scholar
• Huisgen, R.; Fulka, C.; Kalwinsch, I.; Xingya, L.; Mloston, G.; Moran, J. R.; Pröbstl, A. Recent Developments of the Chemistry of Thiocarbonyl Ylides. Bull. Soc. Chim. 1984, 93, 511–532. DOI: 10.1002/bscb.19840930701.
   Google Scholar
• Huisgen, R.; Mloston, G. Adamantanethione and Diazomethane; a Re-Examination. Tetrahedron Lett. 1985, 26, 1049–1052. DOI: 10.1016/S0040-4039(00)98509-5.
   Web of Science ®Google Scholar
• Burdzinski, G.; Sliwa, M.; Zhang, Y.; Delbaere, S.; Pedzinski, T.; Réhault, J. Photochemical Formation of Thiirene and Thioketene in 1,2,3-Thiadiazoles with Phenyl Substituents Studied by Time-Resolved Spectroscopy. Photochem. Photobiol. Sci. 2013, 12, 895–901. DOI: 10.1039/c3pp25453d.
   PubMed Web of Science ®Google Scholar