Dirhodium Tetracarboxylate-promoted Reactions

Dirhodium tetracarboxylates (and related structures) are known to promote a variety of reactions, including CH-insertions and cyclopropanations. This playground has proved valuable for testing various mechanistic concepts ranging from non-statistical dynamic effects to preferential metal dissocation before catalytic cycle closure.

Harrison, J. G.; Gutierrez, O.; Jana, N.; Driver, T. G.; Tantillo, D. J. J. Am. Chem. Soc. 2016, 138, 487-490: "Mechanism of Rh2(II)-Catalyzed Indole Formation: The Catalyst Does Not Control Product Selectivity"

Hare, S. R.; Tantillo, D. J. Chem. Sci. 2017, 8, 1442-1449: "Cryptic Post-Transition State Bifurcations Reduce the Efficiency of Lactone-Forming Rh-Carbenoid C-H Insertions"

Lamb, K. N.; Squitieri, R. A.; Chintala, S. R.; Kwong, A. J.; Balmond, E. I.; Soldi, C.; Dmitrenko, O.; Castineira Reis, M.; Chung, R.; Addison, J. B.; Fettinger, J. C.; Hein, J. E.; Tantillo, D. J.; Fox, J. M.; Shaw, J. T. Chem. Eur. J. 2017, 23, 11843-11855: "Synthesis of Benzodihydrofurans by Asymmetric C–H Insertion Reactions of Donor/Donor Carbenoids"

Nickerson, L. A.; Bergstrom, B. D.; Gao, M.; Shiue, Y.-S.; Laconsay, C. J.; Culberson, M. R.; Knauss, W. A.; Fettinger, J. C.; Tantillo, D. J.; Shaw, J. T. Chem. Sci. 2020, 11, 494-498: "Enantioselective Synthesis of Isochromans and Tetrahydroisoquinolines by C–H Insertion of Donor/Donor Carbenes," featured in SYNFACTS.

Laconsay, C. J.; Tantillo, D. J. ACS Catal. 2021, 11, 829-839: "Metal-Bound or Free Ylides as Reaction Intermediates in Metal-Catalyzed [2,3]-Sigmatropic Rearrangements? It Depends"

Nair, V. N.; Kojasoy, V.; Laconsay, C. J.; Kong, W.;Tantillo, D. J.; Tambar, U. K. J. Am. Chem. Soc. 2021,143, 9016-9025: "Catalyst-Controlled Regiodivergence in Rearrangements of Indole-Based Onium Ylides"

Laconsay, C. J.; Tantillo, D. J. Synthesis 2021, 53, 363-3652: "Melding of Experiment and Theory Illuminates Mechanisms of Metal-Catalyzed Rearrangements: Computational Approaches and Caveats"

 

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