Journal Article10.1021/ACS.JOC.8B02432
Copper-Catalyzed Perfluoroalkylation of Allyl Phosphates with Stable Perfluoroalkylzinc Reagents.
Lihua Liu,Xifei Bao,Hua Xiao,Junlan Li,Feifan Ye,Chaoqin Wang,Qinhua Cai,Shilu Fan,Shilu Fan +8 more
12
TL;DR: Preliminary mechanistic studies reveal that the allyl copper intermediate may be involved in the catalytic cycle, and the reaction proceeds under mild reaction conditions with high efficiency, good functional group tolerance, and high regio- and stereoselectivities.
read more
Abstract: A general and practical method for copper-catalyzed cross-coupling of allyl phosphates with stable perfluoroalkylzinc reagents has been developed. The reaction proceeds under mild reaction conditions with high efficiency, good functional group tolerance, and high regio- and stereoselectivities and provides general, straightforward, and useful access to allyl-perfluoroalkyl compounds. Preliminary mechanistic studies reveal that the allyl copper intermediate may be involved in the catalytic cycle.
read more
Chat with Paper
AI Agents for this Paper
Find similar papers on Google Scholar, PubMed and Arxiv
Write a critical review of this paper
Analyze citations of this paper to find unaddressed research gaps
Citations
Radical Perfluoroalkylation of Aliphatic Substrates
TL;DR: A selection of perfluoroalkylation reactions of aliphatic substrates that display methodological and synthetic amplitude is presented in this article , giving examples of their applications and mechanistic details.
33
Selective Synthesis of Z‐Cinnamyl Ethers and Cinnamyl Alcohols through Visible Light‐Promoted Photocatalytic E to Z Isomerization
TL;DR: This method provides scalable and efficient access to Z -cinnamyl ether and allylic alcohol derivatives in high yields with excellent stereoselectivity and provides a powerful strategy for the selective synthesis of Z -magnolol and honokiol derivatives possessing potential biological activity.
29
Radical Pentafluoroethylation of Unactivated Alkenes Using CuCF2CF3.
Xinkan Yang,Gavin Chit Tsui +1 more
TL;DR: The CuCF2CF3 complex generated from low-cost pentafluoroethane is a convenient and practical source for the CF2 CF3 radical under aerobic conditions at room temperature, offering a new opportunity for copper-mediated radical perfluoroalkylation.
19
Silver-Mediated Perfluoroalkylation of Terminal Alkynes with Perfluoroalkyl Iodides
TL;DR: The silver-mediated perfluoroalkylation reaction based on the addition-elimination process of terminal alkynes which was initiated by perfluoalkyl radical to form C(sp)-RF bond has been developed.
13
Copper-mediated pentafluoroethylation of organoboronates and terminal alkynes with TMSCF3.
TL;DR: The TMSCF3-derived CuCF2CF3 species has been successfully applied in pentafluoroethylation of organoboronates and terminal alkynes by using 1,10-phenanthroline as a ligand andTerminal alkynes can undergo aerobic cross-coupling with the TMS CF2 CF3 species in the absence of additional ligands.
10
References
Fluorine in Pharmaceuticals: Looking Beyond Intuition.
TL;DR: Experimental progress in exploration of the specific influence of carbon-fluorine single bonds on docking interactions is reviewed and complementary analysis based on comprehensive searches in the Cambridge Structural Database and the Protein Data Bank is added.
5.8K
Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).
Jiang Wang,María Sánchez-Roselló,José Luis Aceña,Carlos del Pozo,Alexander E. Sorochinsky,Alexander E. Sorochinsky,Alexander E. Sorochinsky,Santos Fustero,Vadim A. Soloshonok,Vadim A. Soloshonok,Hong Liu +10 more
TL;DR: Introduced to the Market in the Last Decade (2001−2011) Jiang Wang,† María Sańchez-Rosello,́‡,§ Jose ́ Luis Aceña, Carlos del Pozo,‡ and Hong Liu.
4.1K
•Book
Comprehensive asymmetric catalysis
Eric N. Jacobsen,Andreas Pfaltz,尚 山本 +2 more
- 01 Jan 1999
TL;DR: Ohkuma et al. as mentioned in this paper proposed an asymmetric Dihydroxylation process for carbon-Carbon double bonds and showed that it can be used for allylation of C=O.
3.9K
Understanding organofluorine chemistry. An introduction to the C–F bond
TL;DR: Fundamental aspects of the C-F bond are explored to rationalise the geometry, conformation and reactivity of individual organofluorine compounds.
3.3K