Minh, D. M., Gunning, H. E. & Strausz, O. P. Formation and reactions of monovalent carbon Intermediates. I. Photolysis of diethyl mercuribisdiazoacetate. J. Am. Chem. Soc. 89, 6785–6787 (1967).ArticleÂ
Google ScholarÂ
Strausz, O. P., Thap, D. M. & Font, J. Formation and reactions of monovalent carbon intermediates. II. Further studies on the decomposition of diethyl mercurybisdiazoacetate. J. Am. Chem. Soc. 90, 1930–1931 (1968).ArticleÂ
CASÂ
Google ScholarÂ
Strausz, O. P. et al. The formation and reactions of monovalent carbon intermediates. III. The reaction of carbethoxymethyne with olefins. J. Am. Chem. Soc. 96, 5723–5732 (1974).ArticleÂ
CASÂ
Google ScholarÂ
Ruzsicska, B. P., Jodhan, A., Choi, H. K. J., Strausz, O. P. & Bell, T. N. Chemistry of carbynes: reaction of CF, CCl, and CBr with alkenes. J. Am. Chem. Soc. 105, 2489–2490 (1983).ArticleÂ
CASÂ
Google ScholarÂ
Bogoslavsky, B. et al. Do carbyne radicals really exist in aqueous solution? Angew. Chem. Int. Ed. 51, 90–94 (2012).ArticleÂ
CASÂ
Google ScholarÂ
Danovich, D., Bino, A. & Shaik, S. Formation of carbon–carbon triply bonded molecules from two free carbyne radicals via a conical intersection. J. Phys. Chem. Lett. 4, 58–64 (2013).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Li, W. L. et al. Formation and characterization of a BeOBeC multiple radical featuring a quartet carbyne moiety. Angew. Chem. Int. Ed. 59, 6923–6928 (2020).ArticleÂ
CASÂ
Google ScholarÂ
Wang, Z., Jiang, L., Sarró, P. & Suero, M. G. Catalytic cleavage of C(sp2)–C(sp2) bonds with Rh-carbynoids. J. Am. Chem. Soc. 141, 15509–15514 (2019).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Jiang, L., Sarró, P., Teo, W. J., Llop, J. & Suero, M. G. Catalytic alkene skeletal modification for the construction of fluorinated tertiary stereocenters. Chem. Sci. 13, 4327–4333 (2022).ArticleÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Tu, H.-F., Jeandin, A. & Suero, M. G. Catalytic synthesis of cyclopropenium cations with Rh-carbynoids. J. Am. Chem. Soc. 144, 16737–16743 (2022).ArticleÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Wang, Z., Herraiz, A. G., del Hoyo, A. M. & Suero, M. G. Generating carbyne equivalents with photoredox catalysis. Nature 554, 86–91 (2018).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Jiang, L., Wang, Z., Armstrong, M. & Suero, M. G. β-Diazocarbonyl compounds: synthesis and their Rh(II)-catalyzed 1,3 C–H insertions. Angew. Chem. Int. Ed. 60, 6177–6184 (2021).ArticleÂ
CASÂ
Google ScholarÂ
Li, X., Golz, C. & Alcarazo, M. α-Diazo sulfonium triflates: synthesis, structure, and application to the synthesis of 1-(dialkylamino)-1,2,3-triazoles. Angew. Chem. Int. Ed. 60, 6943–6948 (2021).ArticleÂ
CASÂ
Google ScholarÂ
Dong, J. Y. et al. Visible light-induced [3 + 2] cyclization reactions of hydrazones with hypervalent iodine diazo reagents for the synthesis of 1-amino-1,2,3-triazoles. Adv. Synth. Catal. 363, 2133–2139 (2021).ArticleÂ
CASÂ
Google ScholarÂ
Su, Y. L., Dong, K., Zheng, H. & Doyle, M. P. Generation of diazomethyl radicals by hydrogen atom abstraction and their cycloaddition with alkenes. Angew. Chem. Int. Ed. 60, 18484–18488 (2021).ArticleÂ
CASÂ
Google ScholarÂ
Wang, X. et al. Convergent synthesis of 1,4-dicarbonyl Z-alkenes through three-component coupling of alkynes, α-diazo sulfonium triflate, and water. J. Am. Chem. Soc. 144, 4952–4965 (2022).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Das, M., Vu, M. D., Zhang, Q. & Liu, X.-W. Metal-free visible light photoredox enables generation of carbyne equivalents via phosphonium ylide C–H activation. Chem. Sci. 10, 1687–1691 (2019).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Vu, M. D., Leng, W.-L., Hsu, H.-C. & Liu, X.-W. Alkene synthesis using phosphonium ylides as umpolung reagents. Asian J. Org. Chem. 8, 93–96 (2019).ArticleÂ
Google ScholarÂ
Matsumoto, A., Maeda, N. & Maruoka, K. Bidirectional elongation strategy using ambiphilic radical linchpin for modular access to 1,4-dicarbonyls via sequential photocatalysis. J. Am. Chem. Soc. 145, 20344–20354 (2023).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Wiles, R. J. & Molander, G. A. Photoredox-mediated net-neutral radical/polar crossover reactions. Isr. J. Chem. 60, 281–293 (2020).ArticleÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Sharma, S., Singh, J. & Sharma, A. Visible light assisted radical–polar/polar–radical crossover reactions in organic synthesis. Adv. Synth. Catal. 363, 3146–3169 (2021).ArticleÂ
CASÂ
Google ScholarÂ
Rammohan, A., Krinochkin, A. P., Khasanov, A. F., Kopchuk, D. S. & Zyryanov, G. V. Sustainable solvent-free Diels–Alder approaches in the development of constructive heterocycles and functionalized materials: a review. Top. Curr. Chem. 380, 43 (2022).ArticleÂ
CASÂ
Google ScholarÂ
Horibe, T. & Ishihara, K. Initiators for radical cation-induced [2 + 2]- and [4 + 2]-cycloadditions of electron-rich alkenes. Chem. Lett. 49, 107–113 (2020).ArticleÂ
CASÂ
Google ScholarÂ
Okada, Y. & Chiba, K. Redox-tag processes: Intramolecular electron transfer and its broad relationship to redox reactions in general. Chem. Rev. 118, 4592–4630 (2018).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Fontana, A. et al. Volvatellin, caulerpenyne-related product from the sacoglossan Volvatella sp. J. Nat. Prod. 62, 931–933 (1999).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Lenz, C., Boeckler, F., Hübner, H. & Gmeiner, P. Fancy bioisosteres: synthesis, SAR, and pharmacological investigations of novel nonaromatic dopamine D3 receptor ligands. Bioorg. Med. Chem. 13, 4434–4442 (2005).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Durrant, J. D. & McCammon, J. A. Potential drug-like inhibitors of group 1 influenza neuraminidase identified through computer-aided drug design. Comput. Bio. Chem. 34, 97–105 (2010).ArticleÂ
CASÂ
Google ScholarÂ
Zhu, W. et al. A remarkable difference that one fluorine atom confers on the mechanisms of inactivation of human ornithine aminotransferase by two cyclohexene analogues of γ-aminobutyric acid. J. Am. Chem. Soc. 142, 4892–4903 (2020).ArticleÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Wang, F., Xu, X., Yan, Y., Zhang, J. & Yang, Y. Asymmetric total synthesis of montanine-type amaryllidaceae alkaloids. Org. Chem. Front. 11, 668–672 (2024).ArticleÂ
CASÂ
Google ScholarÂ
Choi, G. J., Zhu, Q., Miller, D. C., Gu, C. J. & Knowles, R. R. Catalytic alkylation of remote C–H bonds enabled by proton-coupled electron transfer. Nature 539, 268–271 (2016).ArticleÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Prier, C. K., Rankic, D. A. & MacMillan, D. W. C. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis. Chem. Rev. 113, 5322–5363 (2013).ArticleÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
MacKenzie, I. A. et al. Discovery and characterization of an acridine radical photoreductant. Nature 580, 76–80 (2020).ArticleÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Shang, T.-Y. et al. Recent advances of 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) in photocatalytic transformations. Chem. Commun. 55, 5408–5419 (2019).ArticleÂ
CASÂ
Google ScholarÂ
Neese, F. The ORCA program system. Wiley Interdiscip. Rev. Comput. Mol. Sci. 2, 73–78 (2012).ArticleÂ
CASÂ
Google ScholarÂ
Neese, F. Software update: the ORCA program system—version 5.0. Wiley Interdiscip. Rev. Comput. Mol. Sci. 12, e1606 (2022).ArticleÂ
Google ScholarÂ