TY - JOUR

T1 - Cu-catalyzed cycloaddition of aryl azides to 1-iodobuta-1,3-diynes: an experimental and quantum chemical study of unusual regiochemistry

AU - Govdi, A.I.

AU - Danilkina, N.A.

AU - Shtyrov, A.A.

AU - Ryazantsev, M.N.

AU - Kim, M.D.

AU - Kryukova, M.A.

AU - Balova, I.A.

N1 - Export Date: 11 March 2024 CODEN: NJCHE Адрес для корреспонденции: Balova, I.A.; Institute of Chemistry, Universitetskaya nab. 7/9, Russian Federation; эл. почта: i.balova@spbu.ru Сведения о финансировании: Russian Science Foundation, RSF, 19-73-10077-Π Текст о финансировании 1: This work was funded by the Russian Science Foundation grant 19-73-10077-Π. The authors are grateful to the Magnetic Resonance Research Center, Center for X-ray Diffraction Studies, Center for Chemical Analysis and Materials Research, Thermogravimetric and Calorimetric Research Centre, and Computer Centre (all belonging to Saint Petersburg State University) for the physicochemical and computational studies. Dr A. V. Artem’ev (Nikolaev Institute of Inorganic Chemistry, Novosibirsk, Russia) is thanked for providing the Et catalyst. The authors are grateful to Professor A. F. Khlebnikov (Institute of Chemistry, Saint Petersburg State University, St. Petersburg, Russia) for a constructive discussion. 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PY - 2024

Y1 - 2024

N2 - Cu-catalyzed azide-alkyne cycloaddition (CuAAC) in the case of 1-iodoalkynes is known as a synthetic tool towards 5-iodo-1,2,3-triazole derivatives. We found that CuAAC of 1-iodobuta-1,3-diynes and aryl azides under CuI(PPh3)3 catalysis unexpectedly leads to the formation of both 4-iodo- and 5-iodo-1,2,3-triazoles. Aryl azides bearing acceptor groups and iodoaryldiacetylenes having donor groups shift the isomer ratio in favor of nontrivial 4-iodotriazoles. The reason for the change in the regioselectivity was explained using DFT calculations, which revealed the binuclear nature of the CuAAC transition states (TSs) for iodoalkynes and azides cycloaddition. The regiochemistry of cycloaddition is determined by the type of azide N atom coordinated to the Cu atom and by a spatial arrangement of the binuclear Cu catalyst and alkyne in the TS. In particular in the case of 1-iodobuta-1,3-diynes both regioisomeric TSs have a linear orientation of the alkyne moiety and the I-Cu-P fragment of the binuclear catalyst that makes both N1-Cu (for 5-I-TS) and N3-Cu (for 4-I-TS) coordination possible. The influence of various electronic and stereoelectronic effects established by NBO analysis, as well as NCI interactions, on the stabilization of isomeric TSs in the reactions of aryl/alkyl azides with iodomono- and diacetylenes is discussed. 4-Iodotriazoles are more thermodynamically stable than 5-iodotriazoles, while only the latter form I-N halogen bonds in the solid state. © 2024 The Royal Society of Chemistry

AB - Cu-catalyzed azide-alkyne cycloaddition (CuAAC) in the case of 1-iodoalkynes is known as a synthetic tool towards 5-iodo-1,2,3-triazole derivatives. We found that CuAAC of 1-iodobuta-1,3-diynes and aryl azides under CuI(PPh3)3 catalysis unexpectedly leads to the formation of both 4-iodo- and 5-iodo-1,2,3-triazoles. Aryl azides bearing acceptor groups and iodoaryldiacetylenes having donor groups shift the isomer ratio in favor of nontrivial 4-iodotriazoles. The reason for the change in the regioselectivity was explained using DFT calculations, which revealed the binuclear nature of the CuAAC transition states (TSs) for iodoalkynes and azides cycloaddition. The regiochemistry of cycloaddition is determined by the type of azide N atom coordinated to the Cu atom and by a spatial arrangement of the binuclear Cu catalyst and alkyne in the TS. In particular in the case of 1-iodobuta-1,3-diynes both regioisomeric TSs have a linear orientation of the alkyne moiety and the I-Cu-P fragment of the binuclear catalyst that makes both N1-Cu (for 5-I-TS) and N3-Cu (for 4-I-TS) coordination possible. The influence of various electronic and stereoelectronic effects established by NBO analysis, as well as NCI interactions, on the stabilization of isomeric TSs in the reactions of aryl/alkyl azides with iodomono- and diacetylenes is discussed. 4-Iodotriazoles are more thermodynamically stable than 5-iodotriazoles, while only the latter form I-N halogen bonds in the solid state. © 2024 The Royal Society of Chemistry

KW - Catalysts

KW - Copper compounds

KW - Hydrocarbons

KW - Quantum chemistry

KW - Acceptor groups

KW - Aryl azides

KW - Azide-alkyne cycloaddition

KW - Cycloadditions

KW - Donor groups

KW - Iodoalkynes

KW - Quantum chemical studies

KW - Regiochemistry

KW - Transition state

KW - Triazole derivatives

KW - Catalysis

UR - https://www.mendeley.com/catalogue/53d0dd2b-d93f-33a6-a836-4b9a7eedd8e0/

U2 - 10.1039/d3nj03823h

DO - 10.1039/d3nj03823h

M3 - статья

JO - New Journal of Chemistry

JF - New Journal of Chemistry

SN - 1144-0546

ER -