Molecular Catalysis, Journal Year: 2024, Volume and Issue: 572, P. 114758 - 114758
Published: Dec. 9, 2024
Language: Английский
Molecular Catalysis, Journal Year: 2024, Volume and Issue: 572, P. 114758 - 114758
Published: Dec. 9, 2024
Language: Английский
Chemical Science, Journal Year: 2024, Volume and Issue: 15(30), P. 12026 - 12035
Published: Jan. 1, 2024
A 1,2,3,4-tetrafunctionalization of polyfluoroalkynes for the divergent construction 5-7-membered ( E )-1,2-difluorovinyl azacycles is developed.
Language: Английский
Citations
16Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(22)
Published: March 22, 2024
Abstract The use of gem ‐difluorinated cyclopropanes ( ‐DFCPs) as fluoroallyl surrogates under transition‐metal catalysis has drawn considerable attention recently but such reactions are restricted to producing achiral or racemic mono‐fluoroalkenes. Herein, we report the first enantioselective allylation indoles rhodium with ‐DFCPs. This reaction shows exceptional branched regioselectivity towards ‐DFCPs, which provides an efficient route enantioenriched fluoroallylated wide substrate scope and good functional group tolerance.
Language: Английский
Citations
15Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(11)
Published: Jan. 10, 2024
Here we present a modular, chemo-, regio-, and stereoselective synthesis of fully-substituted configuration-defined alkyl vinyl ethers (AVEs) using simple chemical feedstocks. The distinctive approach involves the chemo- regioselective functionalization CF
Language: Английский
Citations
12Chemical Communications, Journal Year: 2024, Volume and Issue: 60(28), P. 3764 - 3773
Published: Jan. 1, 2024
This feature article summarizes our efforts towards developing Rh-catalyzed reactions of gem -difluorinated cyclopropanes, briefly discussing the design, selectivity, mechanisms and future research prospects.
Language: Английский
Citations
12Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(23)
Published: Feb. 27, 2024
A novel enantioselective Tsuji-Trost-type cross coupling reaction between gem-difluorinated cyclopropanes and N-unprotected amino acid esters enabled by synergistic Pd/Ni/chiral aldehyde catalysis is presented herein. This transformation streamlined the diversity-oriented synthesis (DOS) of optically active α-quaternary α-amino bearing a linear 2-fluoroallylic motif, which served as an appealing platform for construction other valuable enantioenriched compounds. The key intermediates were confirmed HRMS detection, while DFT calculations revealed that excellent enantioselectivity was attributed to stabilizing non-covalent interactions Pd(II)-π-fluoroallyl species Ni(II)-Schiff base complex.
Language: Английский
Citations
11Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)
Published: May 21, 2024
Abstract Transition-metal catalyzed allylic substitution reactions of alkenes are among the most efficient methods for synthesizing diene compounds, driven by inherent preference an inner-sphere mechanism. Here, we present a demonstration outer-sphere mechanism in Rh-catalyzed reaction simple using gem -difluorinated cyclopropanes as allyl surrogates. This unconventional offers opportunity fluorine recycling via C − F bond cleavage/reformation, ultimately delivering carbofluorination products. The developed method tolerates wide range alkenes, providing access to secondary, tertiary fluorides and -difluorides with 100% atom economy. DFT calculations reveal that formation goes through unusual nucleophilic allyl-Rh species instead migration insertion, generated carbon cation then forms tetrafluoroborate fluoride shuttle.
Language: Английский
Citations
9Advanced Science, Journal Year: 2024, Volume and Issue: 11(18)
Published: March 9, 2024
Abstract Transition‐metal (TM) catalyzed reaction of gem ‐difluorinated cyclopropanes ( ‐DFCPs) has drawn much attention recently. The generally occurs via the activation distal C─C bond in ‐DFCPs by a low‐valent TM through oxidative addition, eventually producing mono‐fluoro olefins as coupling products. However, achieving regioselective proximal that overcomes intrinsic reactivity catalysis remains elusive. Here, new mode enabled high‐valent copper catalysis, which allows exclusive congested is presented. achieves fluoroarylation uses NFSI (N‐fluorobenzenesulfonimide) electrophilic fluoro reagent and arenes C─H nucleophiles, enabling synthesis diverse CF 3 ‐containing scaffolds. It proposed species plays an important role possibly σ‐bond metathesis.
Language: Английский
Citations
6Organic Letters, Journal Year: 2023, Volume and Issue: 25(50), P. 9020 - 9024
Published: Dec. 8, 2023
This study presents a novel method for the regioselective coupling of gem-difluorinated cyclopropanes with gem-diborylmethane, utilizing Pd-catalyst system. innovative approach enables synthesis 2-fluoroalkenyl monoboronate scaffolds high Z-selectivity. The resulting products undergo further transformations, including oxidation, Suzuki cross-coupling, and trifluoroborylation, all which are achieved good yields. work introduces valuable synthetic pathway to access important fluorinated compounds various applications in organic chemistry.
Language: Английский
Citations
14Organic Letters, Journal Year: 2024, Volume and Issue: 26(25), P. 5375 - 5379
Published: June 12, 2024
We herein disclose the Pd/amine dual-catalyzed ring-opening cross-coupling reaction between
Language: Английский
Citations
5Chemical Science, Journal Year: 2024, Volume and Issue: 15(34), P. 13800 - 13806
Published: Jan. 1, 2024
Metathesis reactions have been established as a powerful tool in organic synthesis. While great advances were achieved double-bond metathesis, like olefin metathesis and carbonyl single-bond has received less attention the past decade. Herein, we describe first C(sp
Language: Английский
Citations
5