Olefination of Activated Alkyl Halides with Phosphonium Salts DOI
Sven Roediger, Adriana Neves Vieira, Bill Morandi

et al.

Synthesis, Journal Year: 2024, Volume and Issue: 56(24), P. 3923 - 3928

Published: Nov. 7, 2024

Abstract A base-promoted olefination reaction between alkylphosphonium salts and activated alkyl halides has been developed. The products were obtained in excellent E-selectivity. In contrast to most other reactions of phosphonium salts, the yields triphenylphosphine as main by-product, which can be directly reused formation new salts.

Language: Английский

Enantioselective Borylative Functionalization of Internal Alkenes: A Platform for Constructing Vicinal Stereocenters† DOI
Yu‐Jie Zhu, Jiaxin Li, Haotian Zhao

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(24), P. 3588 - 3604

Published: Nov. 1, 2024

Comprehensive Summary Vicinal stereogenic centers are ubiquitous structural scaffolds in both natural products and synthetic compounds, yet their enantioselective construction remains a significant challenge organic synthesis. Organoboron compounds of paramount importance chemistry due to ability undergo facile transformations, yielding diverse essential chemical bonds such as carbon‐carbon, carbon‐oxygen, carbon‐nitrogen, carbon‐halogen bonds. Transition‐metal‐catalyzed asymmetric borylative functionalizations internal alkenes offer promising strategy for the installation two adjacent chiral across carbon‐carbon By leveraging versatile transformations newly introduced boryl unit, this approach holds great potential expanding diversity vicinal scaffolds. In concise review, we aim highlight recent advancements transition‐metal‐catalyzed alkenes, underscore utility constructing centers, discuss unsolved challenges future directions field. Key Scientists

Language: Английский

Citations

4
Enantioselective Aminosilylation of Alkenes by Palladium/Ming‐Phos‐Catalyzed Tandem Narasaka–Heck/Silylation Reaction DOI Creative Commons

Kangning Cao,

Jie Han, Wenshao Ye

et al.

Advanced Science, Journal Year: 2024, Volume and Issue: unknown

Published: July 5, 2024

A Pd-catalyzed enantioselective aminosilylation of alkenes via tandem Aza-Heck/silylation reaction under Pd/Sadphos catalysis is disclosed. wide array oxime esters and silicon reagents are tolerated, furnishing the chiral pyrrolines bearing one quaternary or two contiguous stereocenters in good yield with high enantioselectivity. Not only terminal but also tri-substituented internal successfully participate reaction, delivering vicinal complete diastereoselectivity DFT study conducted to probe pathway origin enantioselectivity, which revealed that stereoinduction arises from weak interaction between aromatic ring substrate fragment naphthyl group ligand.

Language: Английский

Citations

3
Enantioselective Copper-Catalyzed Three-Component Cascade Boronation–Dearomatization Reaction: Synthesis of Chiral Boron-Containing 1,4-Dihydropyridines DOI

Fazhou Yang,

Yujie Dong, Jinbao Wang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 10, 2025

A three-component cascade boronation–dearomatization reaction of alkenes, a diboron compound, and pyridinium salt is diclosed, affording chiral boron-containing 1,4-dihyropyridines in high yields (≤98%) diastereoselectivity (≤10:1 dr), along with excellent enantioselectivity (typically >99% ee). The catalytic system performs efficiently at low catalyst loadings (1 mol %) was tested >50 examples, including some biologically active molecules.

Language: Английский

Citations

0
CuH-Catalyzed Regio- and Stereoselective Hydroalkoxylation of Styrenes with Acetal-Based Peroxides DOI
Shōgo Nakamura,

Kyosuke Fujiwara,

Yuki Kojima

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 8353 - 8360

Published: May 5, 2025

Language: Английский

Citations

0
Radical Arylboration of Unactivated Alkenes via Visible-Light Catalysis DOI
Xiaoyu Li, Menglin Yang, Simin Wang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 7, 2025

A photoinduced radical arylboration of unactivated alkenes with B2pin2 and aryl nitriles was developed, providing a mild efficient approach to access useful β-aryl boronates in the absence transition-metal catalyst. This reaction undergoes boron addition alkene subsequent radical-radical coupling process. showcases good functional group compatibility provides promising complementary strategy chemistry traditional transition-metal-catalyzed coupling.

Language: Английский

Citations

0
Copper-catalyzed enantioselective three-component radical 1,4-perfluoroalkylamination of 1,3-dienes DOI Creative Commons

Xiaoyan Shangguan,

Lihan Zhu, Y.‐W. ZHANG

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: May 28, 2025

Language: Английский

Citations

0
Enantio- and E-Selective Copper-Catalyzed Three-Component Hydrofunctionalization of Internal Allenes Bearing Methylidenecyclobutanes with Diborons and Ketones DOI
Yujie Dong,

Nianci Zhang,

Rongjin Ning

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: June 5, 2025

Internal allenes are challenging substrates in copper-catalyzed borylative difunctionalization. When internal featuring a methylidenecyclobutane motif were employed, hydrofunctionalization reaction using diborons and ketones as partners the presence of chiral monophosphorus ligand was developed, affording series unsaturated tertiary alcohols preserving high regio- stereoselectivities. Control experiments suggest that involves boronation-deboronation process, plausible mechanism has been proposed.

Language: Английский

Citations

0
Synthesis of axially chiral thiourea by NHC-catalyzed desymmetrizative amidation DOI

Yingtao Wu,

Xin Guan,

Kehan Jiao

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

NHC-catalyzed desymmetrization amidation of biaryl dialdehydes has been developed for NH-free axially chiral thiourea. Sequential kinetic resolution enhances the chirality induction strategy, expanding applicable scope.

Language: Английский

Citations

0
Olefination of Activated Alkyl Halides with Phosphonium Salts DOI
Sven Roediger, Adriana Neves Vieira, Bill Morandi

et al.

Synthesis, Journal Year: 2024, Volume and Issue: 56(24), P. 3923 - 3928

Published: Nov. 7, 2024

Abstract A base-promoted olefination reaction between alkylphosphonium salts and activated alkyl halides has been developed. The products were obtained in excellent E-selectivity. In contrast to most other reactions of phosphonium salts, the yields triphenylphosphine as main by-product, which can be directly reused formation new salts.

Language: Английский

Citations

0