Overclocking Nitronyl Nitroxide Gold Derivatives in Cross‐Coupling Reactions

Overclocking Nitronyl Nitroxide Gold Derivatives in Cross‐Coupling Reactions Full article

Journal

Chemistry - A European Journal
ISSN: 0947-6539 , E-ISSN: 1521-3765

Output data

Year: 2023, Volume: 29, Number: 6, Article number : e202203118, Pages count : DOI: 10.1002/chem.202203118

Tags

molecular magnets new reagent design nitronyl nitroxides radical reactions thermal stability

Authors

Zayakin Igor ¹ , Tretyakov Evgeny ¹ , Akyeva Anna ¹ , Syroeshkin Mikhail ¹ , Burykina Julia ¹ , Dmitrenok Andrey ¹ , Korlyukov Alexander ² , Nasyrova Darina ¹ , Bagryanskaya Irina ³ , Stass Dmitri ⁴ , Ananikov Valentine ¹

Affiliations

1	Федеральное государственное бюджетное учреждение науки Институт органической химии им. Н.Д. Зелинского Российской академии наук
2	A.N.Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
3	N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of Siberian Branch of Russian Academy of Sciences
4	Voevodsky Institute of Chemical Kinetics and Combustion, SB RAS

Nitronyl nitroxides are functional building blocks in cutting-edge research fields, such as the design of molecular magnets, the development of redox and photoswitchable molecular systems and the creation of redox-active components for organic and hybrid batteries. The key importance of the nitronyl nitroxide function is to translate molecular-level-optimized structures into nano-scale devices and new technologies. In spite of great importance, efficient and versatile synthetic approaches to these compounds still represent a challenge. Particularly, methods for the direct introduction of a nitronyl nitroxide moiety into aromatic systems possess many limitations. Here, we report gold derivatives of nitronyl nitroxide that can enter Pd(0)-catalysed cross-coupling reactions with various aryl bromides, affording the corresponding functionalized nitronyl nitroxides. Based on the high thermal stability and enhanced reactivity in catalytic transformation, a new reagent is suggested for the synthesis of radical systems via a universal cross-coupling approach.

Zayakin I. , Tretyakov E. , Akyeva A. , Syroeshkin M. , Burykina J. , Dmitrenok A. , Korlyukov A. , Nasyrova D. , Bagryanskaya I. , Stass D. , Ananikov V.
Overclocking Nitronyl Nitroxide Gold Derivatives in Cross‐Coupling Reactions
Chemistry - A European Journal. 2023. V.29. N6. e202203118 . DOI: 10.1002/chem.202203118 WOS РИНЦ

Submitted:	Oct 6, 2022
Accepted:	Oct 19, 2022
Published print:	Dec 7, 2022
Published online:	Jan 27, 2023

Web of science	WOS:000893567300001
Elibrary	59511422
OpenAlex	W4306777642