A visible-light-induced and iron-catalyzed methylation of arylacrylamides by dimethyl sulphoxide (DMSO) is achieved, leading to 3-ethyl-3-methyl indolin-2-ones in high yields. This reaction tolerates a series of functional groups, such as methoxy, trifluoromethyl, cyano, nitro, acetyl and ethyloxy carbonyl groups. The visible-light promoted radical methylation and arylation of the alkenyl group are involved in this reaction.
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http://dx.doi.org/10.1039/c7ob00779e | DOI Listing |
Org Lett
August 2024
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Frontiers Science Center for New Organic Matter, Nankai University, Tianjin 300071, China.
Four-membered ring structure is important in organic chemistry, and selective cleavage and functionalization of these strained rings are of great interest. However, direct α-functionalization of cyclobutanols is rarely reported because of the high O-H bond dissociation energy and the occurrence of β-scission of C-C bonds in these alcohols. Recently, transition-metal catalysis has facilitated alkoxy radical generation.
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April 2024
Normandie Univ., LCMT, ENSICAEN, UNICAEN, CNRS, 6 boulevard du Maréchal Juin, 14000, Caen, France.
A visible-light-induced iron-catalyzed α-alkylation of ketones with allylic and propargylic alcohols as pro-electrophiles is reported. The diaminocyclopentadienone iron tricarbonyl complex plays a dual role by harvesting light and facilitating dehydrogenation and reduction steps without the help of any exogenous photosensitizer. γ,δ-Unsaturated ketones can now be accessed through this borrowing hydrogen methodology at room temperature.
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November 2023
State Key Laboratory of Fine Chemicals, Frontier Science Center for Smart Materials, Dalian University of Technology, Dalian 116024, China.
An efficient visible-light-induced iron-catalyzed reduction of nitroarenes to anilines by using -ethylmorpholine (NEM) as a reductant under mild conditions has been developed. The reaction proceeds with photosensitizer-free conditions and features good to excellent yields and broad functional group tolerance. Preliminary mechanistic investigations showed that this reaction was conducted ligand-to-metal (NEM to Fe) charge transfer and nitro triplet biradical-induced hydrogen atom transfer processes.
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September 2022
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Frontiers Science Center for New Organic Matter, Tianjin 300071, People's Republic of China.
Alkynylsilanes are one kind of essential synthetic block in organic chemistry. The established synthetic routes retain some drawbacks regarding harsh reaction conditions or expensive/rare metal catalysts. Herein, we report a method for iron-catalyzed, visible-light-induced alkynylation of hydrosilanes to produce value-added silicon compounds.
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October 2022
Lehn Institute of Functional Materials, School of Chemistry, Sun Yat-sen University, Guangzhou, 510006, P. R. China.
An iron-catalyzed remote C(sp )-H amination of alcohols through 1,5-hydrogen atom transfer is developed. This protocol provides a method to generate δ-C(sp )-N bonds from primary, secondary, and tertiary alcohols under mild conditions. A wide substrate scope and a good functional group tolerance are presented.
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