A visible-light induced three-component reaction of difluoroalkyl halides, unactivated alkenes, and alkynyl sulfones is described, providing a direct and general approach to the construction of synthetically valuable β-difluoroalkylated alkynes under room temperature conditions. This represents the first intermolecular alkynyl-difluoroalkylation of unactivated alkenes.
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http://dx.doi.org/10.1039/c8cc03105c | DOI Listing |
Angew Chem Int Ed Engl
January 2025
Zhejiang Uiversity, Chemistry, 866 Yuhangtang Road, 310058, Hangzhou, CHINA.
Heck silylation of unactivated alkenes is an efficient strategy for the synthesis of useful organosilicon compounds. However, extensive efforts have been dedicated to only achieving achiral molecules. Herein, a highly regio- and enantioselective cobalt-catalyzed Heck silylation of unactivated alkenes with hydrosilanes is reported for the first time, providing access to axially chiral alkenes in good to excellent yields with 87-98% ee.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Advanced Catalysis and Green Manufacturing Collaborative Innovation Center, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China.
A visible-light-promoted azidation/arylation of unactivated alkenes with Togni-N has been achieved, leading to a series of azidated pyrrolo[1,2-]indoles under photocatalyst-free conditions. Notably, an EDA complex derived from the electron-rich indole derivatives and Togni-N served as the key intermediate in this reaction.
View Article and Find Full Text PDFOrg Lett
January 2025
State Key Laboratory of Microbial Technology, Shandong University, 72 Binhai Road, Qingdao, Shandong 266237, P. R. China.
An anaerobic 1,2-/1,3-hydroxytrifluoromethylation of unactivated alkenes is described. This reaction proceeds in mild and environmentally friendly conditions without photocatalyst and metal catalyst, allowing access to a wide range of β- and γ-trifluoromethyl alcohols. Preliminary mechanistic investigations indicate that the accomplishment of this protocol relies on the dual functionality of the photoexcited triplet nitroarenes, which serve as the oxygen atom source and enable the single-electron transfer (SET) process with CFSONa.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, United States.
We report a Ni-catalyzed vicinal alkylarylation of unactivated alkenes in γ,δ- and δ,ε-alkenylamines with aryl halides and alkylzinc reagents. The reaction is enabled by amine coordination and can use all primary, secondary, and tertiary amines. The reaction constructs two new C(sp)-C(sp) and C(sp)-C(sp) bonds and produces δ- and ε-arylamines with C(sp)-branching at the γ- and δ-positions.
View Article and Find Full Text PDFJ Org Chem
January 2025
Department of Chemistry, Malaviya National Institute of Technology Jaipur, Jaipur 302017, Rajasthan, India.
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