Diastereoselective Homocoupling of Benzylic C(sp3)–H Bonds Enabled by Halogen Transfer DOI
Xirong Liu, Xin An, Xue Zhao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(43), P. 9257 - 9262

Published: Oct. 18, 2024

A transition-metal- and harsh-oxidant-free strategy for diastereoselective homocoupling of benzylic α-boryl carbanions has been developed. Central to this methodology is the ability halogen transfer reagent seamlessly integrate halogenation substitution within a compatible process. Additionally, also applicable diarylmethanes alkylheteroarenes. Substrates bearing oxidatively sensitive functional groups were well-tolerated. Preliminary studies suggest that hydrogen bond between two boryl contributes high diastereoselectivities.

Language: Английский

Synthesis of Monofluorocyclohexene via Photocatalytic Defluorinative [4+2] Annulation of gem‐Difluoroalkenes with Unactivated Alkenes DOI

Guangxu Zhang,

Dong‐Sheng Li, Fei Xue

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(24), P. 4603 - 4608

Published: Nov. 1, 2023

Abstract Herein, a photocatalytic system for defluorinative [4+2] annulation of gem ‐difluoroalkenes with unactivated alkenes is realized. This protocol was compatible broad scope alkenes, affording the diverse monofluorocyclohexene products in 30–95% yields. Furthermore, value this method demonstrated by gram‐scale synthesis, late‐stage functionalization and synthesis various valuable complex derivatives.

Language: Английский

Citations

3

Photoinduced Generation of Active Intermediates from Unmodified 1,3‐Dicarbonyl Compounds for Organic Transformations DOI
Haoyuan Li, Xiaoying Niu, Xiu‐Long Yang

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(14)

Published: March 6, 2024

Abstract Photocatalysis utilizes light as the initial driving force for chemical reactions, enabling reactions with high energy barriers in traditionally thermal chemistry to proceed under mild conditions. 1,3‐Dicarbonyl compounds occur important active molecules nature and are intermediates pharmaceutical syntheses. In recent years, there have been numerous studies of these compounds, it is common practice pre‐modify them before reaction, which is, however, unfavorable atom economy process. This paper provides a comprehensive review latest advancements site‐specific activation unmodified 1,3‐dicarbonyl by photoinduction. The focus on elucidating mechanisms provide insights directions future research designing novel reactions.

Language: Английский

Citations

0

Biomimetic Photoexcited Cobaloxime Catalysis in Organic Synthesis DOI Creative Commons
Phong Dam, Kaiming Zuo, Luis Miguel Azofra

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: May 22, 2024

Abstract Drawing inspiration from nature has long been a cornerstone of chemical innovation, with natural systems offering wealth untapped potential for discovery. In this minireview, we delve into the burgeoning field cobaloxime catalysis in organic synthesis, which mimics catalytic activity organometallic alkylcobalamine enzymes. Our focus lies on elucidating latest advancements area, as well delineating primary mechanistic pathways at play. By describing, and comparing these mechanisms, provide comprehensive overview current state‐of‐the‐art, while also shedding light key unresolved challenges that await further exploration.

Language: Английский

Citations

0

Construction of Quaternary Alkyl Motifs through Palladium- Catalyzed Oxidative Coupling of 1,3-Dicarbonyl Compounds with Alkenes Followed by C-C Bond Cleavage DOI
Xu Zhang,

Mengfan Chang,

Tongtong Ni

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(78), P. 10958 - 10961

Published: Jan. 1, 2024

A palladium-catalyzed coupling reaction has been developed for the generation of tertiary alkylation products by reacting olefins with diversely functionalized 1,3-dicarbonyls. The involves C-H 1,3-dicarbonyls to produce a alcohol, followed C-C bond cleavage.

Language: Английский

Citations

0

Diastereoselective Homocoupling of Benzylic C(sp3)–H Bonds Enabled by Halogen Transfer DOI
Xirong Liu, Xin An, Xue Zhao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(43), P. 9257 - 9262

Published: Oct. 18, 2024

A transition-metal- and harsh-oxidant-free strategy for diastereoselective homocoupling of benzylic α-boryl carbanions has been developed. Central to this methodology is the ability halogen transfer reagent seamlessly integrate halogenation substitution within a compatible process. Additionally, also applicable diarylmethanes alkylheteroarenes. Substrates bearing oxidatively sensitive functional groups were well-tolerated. Preliminary studies suggest that hydrogen bond between two boryl contributes high diastereoselectivities.

Language: Английский

Citations

0