On the role of thermally activated EDA complexes in decarboxylative cross-coupling DOI

Nathan Dao,

Ryan A. Shenvi

Tetrahedron, Journal Year: 2024, Volume and Issue: 166, P. 134204 - 134204

Published: Aug. 17, 2024

Language: Английский

Bimolecular Homolytic Substitution (SH2) at A Transition Metal DOI
Ying Zhang, Kai‐Dian Li, Huan‐Ming Huang

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: 16(21)

Published: Aug. 8, 2024

Abstract Transition metal‐catalyzed cross‐coupling reactions have become a powerful and widely used synthetic approach for the construction of both carbon‐carbon carbon‐heteroatom bonds. These revolutionized chemistry by enabling efficient formation complex molecular architectures. Among various methods available, bimolecular homolytic substitution (S H 2) reaction has emerged as an attractive versatile method C(sp 3 )−C(sp ) )‐heteroatom In recent years, significant progress been made in development radical S 2 reactions, particularly those involving different transition metal complexes such cobalt, nickel, iron. advancements expanded scope allowing greater diversity substrate compatibility conditions. this review, we aim to highlight latest breakthroughs mechanistic insights into focusing on role catalysts facilitating these transformations. We will discuss types that employed, pathways involved, potential applications synthesis organic molecules.

Language: Английский

Citations

1

Nickel‐Catalyzed α‐selective Hydroalkylation of Vinylarenes DOI
Jia‐Wang Wang,

Qingwei Zhu,

Deguang Liu

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(47)

Published: Aug. 12, 2024

C(sp

Language: Английский

Citations

1

Iron‐Catalyzed Regioselective Borobenzylation of Vinyl Arenes DOI Open Access

Deyuan Meng,

Jaesook Yun

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(24), P. 5061 - 5065

Published: Aug. 27, 2024

Abstract Herein, catalytic difunctionalization of vinyl arenes is reported using an iron salt as a catalyst without ligands. A series substituted alkylboronic acid esters was obtained single regioisomer from at 50 °C. This multicomponent protocol enabled the formation C−C and C−B bonds to produce boroalkylated products in process. non‐radical pathway proposed for reaction contrast radical pathways iron‐catalyzed hydroalkylation reactions. The organoboron compounds generated this were further utilized diverse functional group conversions.

Language: Английский

Citations

1

Reductive Olefin Bicyclo[1.1.0]butane Coupling Enabled by Iron Hydride Hydrogen Atom Transfer DOI
Guang Chen,

Dayu Tian,

Xiaocheng Wang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 14928 - 14936

Published: Sept. 25, 2024

Language: Английский

Citations

1

Recent Advances in Nonprecious Metal Catalysis DOI
David J. Bernhardson, Aran K. Hubbell, Robert A. Singer

et al.

Organic Process Research & Development, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 7, 2024

As the field of nonprecious metal catalysis continues to expand, we pursue a review series covering selected transformations in this area over short time interval highlight practical advancements. We seek raise awareness both current art and need continue development toward broader applications earth-abundant metals chemical pharmaceutical industries.

Language: Английский

Citations

1

Cost‐Effective Carbon Quaternization with Redox‐Active Esters and Olefins DOI

Sudhir Kumar Hota,

Sandip Murarka

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(41)

Published: July 10, 2024

Abstract Quaternary carbons are embedded in various natural products, pharmaceuticals, and organic materials. However, constructing this valuable motif is far from trivial. Conventional approaches mainly rely on classical polar disconnections encounter bottlenecks concerning harsh conditions, functional group tolerance, regioselectivity, step economy. In context, Kawamata, Baran, Shenvi, co‐workers recently demonstrated that two feedstock chemicals, alkyl carboxylic acids olefins, could be utilized to construct tetrasubstituted the presence of an inexpensive iron porphyrin catalyst a suitable reductant combination through quaternization radical intermediates. The method enables access sterically encumbered quaternary under mild robust conditions. Taking complete detour conventional approaches, present heteroselective radical–radical coupling simplifies synthesis carbon‐containing molecules innovative distinctive disconnection approach.

Language: Английский

Citations

0

Reductive Electrophilic Cross-Coupling for Constructing C(sp3)–C(sp3) Bonds DOI
Pengfei Li, Youai Qiu

Synlett, Journal Year: 2024, Volume and Issue: unknown

Published: July 25, 2024

Abstract The C(sp3)–C(sp3) bond is one of the most prevalent motifs in organic compounds and holds significant importance synthesis. utilization two alkyl electrophiles for cross-coupling stands as a vital strategy building bonds. Nowadays, synthetic electrochemistry undergoing rapid development owing to its exceptional attributes not only terms green economic properties by reducing large amount traditional chemical reductants, but also capacity generate highly reactive radical intermediates under mild conditions, thereby opening up new reaction pathways presenting novel opportunities constructing This article aims comprehensively delineate historical electrophilic reagents bonds, while delving into advantages electrochemical this domain. 1 Introduction 2 Case Studies Nickel-Catalyzed Photochemical Alkyl Halide Cross-Coupling 3 Electrocatalyzed Approaches Construction Bonds Using Electrophilic Reagents 4 Nickel-Electrocatalyzed Unactivated Halides 5 Conclusion

Language: Английский

Citations

0

Nickel‐Catalyzed α‐selective Hydroalkylation of Vinylarenes DOI
Jia-Wang Wang,

Qingwei Zhu,

Deguang Liu

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(47)

Published: Aug. 12, 2024

Abstract C( sp 3 ) centers adjacent to (hetero) aryl groups are widely present in physiologically active molecules. Metal‐hydride‐catalyzed hydroalkylation of alkenes represents an efficient means forging )−C( bonds, boasting advantages as a wide source substrates, mild reaction conditions, and facile selectivity manipulation. Nevertheless, the vinylarenes encounters constraints terms substrate scope, necessitating employment activated alkyl halides or containing chelating groups, remains challenge. In this context, we report general nickel‐hydride‐catalyzed protocol for vinylarenes. Remarkably, system enables α‐selective both heteroaryl under extra ligand‐free condition, demonstrating excellent coupling efficiency selectivity. Furthermore, through incorporation chiral bisoxazoline ligands, have achieved regio‐ enantioselective vinylpyrroles, thereby facilitating synthesis α‐branched alkylated pyrrole derivatives.

Language: Английский

Citations

0

On the role of thermally activated EDA complexes in decarboxylative cross-coupling DOI

Nathan Dao,

Ryan A. Shenvi

Tetrahedron, Journal Year: 2024, Volume and Issue: 166, P. 134204 - 134204

Published: Aug. 17, 2024

Language: Английский

Citations

0