Photocatalyzed H2-Acceptorless Dehydrogenative Borylation by Using Amine Borane DOI
Haowen Jiang,

Wan‐Lei Yu,

Dong Wang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(11), P. 8666 - 8675

Published: May 20, 2024

Catalytic dehydrogenative borylation of alkenes is arguably the most straightforward approach for synthesizing alkenyl boronates, as it eliminates need alkene or boranes prefunctionalizion. While transition-metal catalysis has conventionally been employed this transformation, competitive side reactions including hydroborylation, overborylation, and regioisomer formation always exist. In study, we present a radical catalytic borylation, which involves synergistic merger photoredox/HAT/cobalt catalysis, thereby circumventing necessity noble metals, sacrificial hydrogen acceptors, high temperatures. This method employs stable cost-effective amine borane reagents feedstocks, resulting in sole byproduct H2. methodology facilitates conversion diverse array functionalized into valuable organoboron reagents. Furthermore, late-stage complex molecules demonstrates levels site selectivity.

Language: Английский

Ni-Catalyzed Radical-Promoted Defluoroalkylborylation of Trifluoromethyl Alkenes To Access gem-Difluorohomoallylic Boronates DOI

Jian Qiu,

Cece Wang,

Zhou Lü

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(12), P. 2446 - 2451

Published: March 21, 2022

gem-Difluoroalkenyl boronates are attractive synthons for constructing diverse gem-difluoroalkenes and organoboron compounds. However, the strategies construction of gem-difluorohomoallyl has scarcely been described. Herein, we develop an efficient protocol gem-difluorohomoallylic through a Ni-catalyzed radical-promoted defluoroalkylborylation α-trifluoromethyl alkenes with α-haloboronates under mild conditions. This reaction features broad substrate scope good functional group tolerance transformations.

Language: Английский

Citations

43
Photocatalyst-free, metal-free, visible light-induced thiolation/pyridylation of styrenes using an electron donor–acceptor complex as a bifunctional reagent DOI
Jiaxuan Shen, Jincan Li, Meijun Chen

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(5), P. 1166 - 1172

Published: Jan. 1, 2023

Visible light-induced intermolecular thiolation/pyridylation of styrenes using a thiolate-based EDA complex as bifunctional reagent under mild conditions free photocatalyst, metal or external redox agent is reported.

Language: Английский

Citations

26
Diastereoselective Synthesis of Monofluorocyclohexenes through Photocatalyzed Cascade Cyclization of gem‐Difluoroalkenes and α,β‐Unsaturated Carbonyl Compounds DOI
Zhengyu Li, Yizhi Zhang, Yunxiao Zhang

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(20)

Published: March 16, 2023

Monofluoroalkenes are nonhydrolyzable mimetics of amides. Previous work focused on the synthesis non-cyclic monofluoroalkenes. However, diastereoselective monofluorocyclohexenes from substrates is challenging. Herein, we report first photocatalyzed cascade cyclization reactions readily available α,β-unsaturated carbonyl compounds and gem-difluoroalkenes for highly functionalized monofluorocyclohexenes. The reaction shows broad substrate scope with high diastereoselectivity (>30 examples, up to 86 % yield, >20 : 1 dr). post-reaction transformations products demonstrate synthetic potential this methodology.

Language: Английский

Citations

24
Halogen‐Atom Transfer Enabled Catalytic Enantioselective Coupling to Chiral Trifluoromethylated Alkynes via Dual Nickel and Photocatalysis DOI

Shanya Lu,

Zihao Hu,

Dong Wang

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(28)

Published: April 15, 2024

With halogen-atom transfer as an effective tool, a novel catalytic enantioselective protocol to generate chiral trifluoromethylated alkynes has been established by cooperative photoredox and nickel catalysis system, providing straightforward modular route access this type of product in good yields enantioselectivities. The process is essential for the reaction strategy offers another promising way utilize alkyl halides with highly negative reduction potentials. It firstly expands nickel-catalyzed asymmetric reductive cross-couplings organohalides from traditional single-electron transfer.

Language: Английский

Citations

11
Photocatalyzed H2-Acceptorless Dehydrogenative Borylation by Using Amine Borane DOI
Haowen Jiang,

Wan‐Lei Yu,

Dong Wang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(11), P. 8666 - 8675

Published: May 20, 2024

Catalytic dehydrogenative borylation of alkenes is arguably the most straightforward approach for synthesizing alkenyl boronates, as it eliminates need alkene or boranes prefunctionalizion. While transition-metal catalysis has conventionally been employed this transformation, competitive side reactions including hydroborylation, overborylation, and regioisomer formation always exist. In study, we present a radical catalytic borylation, which involves synergistic merger photoredox/HAT/cobalt catalysis, thereby circumventing necessity noble metals, sacrificial hydrogen acceptors, high temperatures. This method employs stable cost-effective amine borane reagents feedstocks, resulting in sole byproduct H2. methodology facilitates conversion diverse array functionalized into valuable organoboron reagents. Furthermore, late-stage complex molecules demonstrates levels site selectivity.

Language: Английский

Citations

11