Nickel-Catalyzed Synthesis of chiral N-Heterocycles via C(sp3)–H Activation of Formamides DOI
Mark A. Reed, M. A. Jalil Miah

Synfacts, Journal Year: 2022, Volume and Issue: 19(01), P. 0016 - 0016

Published: Dec. 16, 2022

Key words formamides - acetylenes Ni–Al-bimetallic catalysis C–H functionalization cyclization N-heterocycles

Language: Английский

Aluminum-Containing Heterobimetallic Complexes as Versatile Platforms for Homogeneous Catalysis DOI
Roushan Prakash Singh, Soumen Sinhababu, Neal P. Mankad

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(19), P. 12519 - 12542

Published: Sept. 11, 2023

Within the broader area of heterobimetallic catalysis, Al/M compounds (M = any metal) are promising for design and execution catalytic manifolds. This Perspective reviews recent advances in focusing on their applications. Topics include polymerization, epoxide activation carbonylation, C–H functionalization, other important transformations mediated by catalysts. In each case, mechanistic role aluminum site is highlighted. A broad range Al-containing metalloligands combinations included to construct this comprehensive perspective.

Language: Английский

Citations

25
Nickel-Catalyzed Atroposelective C–H Alkylation Enabled by Bimetallic Catalysis with Air-Stable Heteroatom-Substituted Secondary Phosphine Oxide Preligands DOI
Zijing Zhang,

Matthias M. Simon,

Shuang Yu

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(13), P. 9172 - 9180

Published: March 21, 2024

The catalytic asymmetric construction of axially chiral C–N atropisomers remains a formidable challenge due to their low rotational barriers and is largely reliant on toxic, cost-intensive, precious metal catalysts. In sharp contrast, we herein describe the first nickel-catalyzed atroposelective C–H alkylation for compounds with aid heteroatom-substituted secondary phosphine oxide (HASPO)-ligated Ni–Al bimetallic catalyst. A wide range alkenes, including terminal internal were well compatible reaction, providing variety benzimidazole derivatives in high yields enantioselectivities (up 97:3 e.r.). key success was identification novel HASPOs as highly effective preligands. Mechanistic studies revealed catalyst mode action, in-depth data science analysis elucidated features responsible preligands controlling enantioselectivity.

Language: Английский

Citations

13
Pd/Chiral Phosphoric Acid-Enabled Asymmetric Intramolecular Double C–H Activation Reaction for the Synthesis of P-Stereogenic Benzophosphole Oxides DOI

Shaobai Yan,

Zhen Li,

Hu XianQi

et al.

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

Published: Feb. 2, 2025

A Pd-catalyzed intramolecular asymmetric double C-H activation reaction was reported, and a BINOL skeleton-based chiral phosphoric acid (CPA) identified as suitable ligand for this transformation. broad range of P-stereogenic benzophosphole oxides were synthesized in moderate to excellent yield with high levels enantioselectivity (≤96% ee).

Language: Английский

Citations

1
Enantioselective C–H annulations enabled by either nickel- or cobalt-electrocatalysed C–H activation for catalyst-controlled chemodivergence DOI Creative Commons
Tristan von Münchow, Neeraj Kumar Pandit, Suman Dana

et al.

Nature Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: March 7, 2025

Language: Английский

Citations

1
Ni‐SPO‐Al Catalyzed Stereoselective C–H Alkenylation of Quinazolinones with Alkynes to Prepare trans‐Isomers DOI
Yaqi Zhang,

Qiang Ni,

Rihui Cao

et al.

European Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 28(5)

Published: Jan. 4, 2025

Abstract A stereoselective Ni−Al bimetal‐catalyzed C−H alkenylation of quinazolinones with alkynes has been successfully developed. Good selectivity Z‐type quinazolinone products was obtained using readily available substrates, which exhibits a trans‐configuration opposite to the conventional alkynylation reactions and improves diversity compounds. In addition, reaction process further explored through KIE other control experiments, possible mechanism proposed.

Language: Английский

Citations

0
New reactivity of late 3d transition metal complexes in catalytic reactions of alkynes DOI
Shenghan Teng,

Peiyao Liang,

Jianrong Steve Zhou

et al.

Chemical Society Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This review summarizes seven types of new reactivities found in late 3d metal complexes and catalytic examples recent years.

Language: Английский

Citations

0
Photocatalytic Pyridyl-carbamoylation of Alkenes for Accessing β-Pyridyl Amides DOI
Jian Cui, Zhikai Li, Yun Mao

et al.

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

Published: March 7, 2025

The β-pyridyl amide is a critical scaffold in medical discovery yet lacks efficient synthetic methods. Here, we describe, for the first time, visible-light-induced, redox-neutral radical cross-coupling reaction involving alkenes, oxamic acids, and cyanopyridines that offers versatile assembly of β-pyridylamides. This approach features mild conditions, high step efficiency, substrate breadth, providing green strategy alkene pyridyl-carbamoylation. Achieving this transformation relies on catalytic system, which adeptly avoids competing nucleophilic carbamoyl with electrophilic pyridyl radical, enabling three-component tandem process chemoselectivity.

Language: Английский

Citations

0
Intermolecular Carbophosphination of Alkynes with Phosphole Oxides via Ni−Al Bimetal‐Catalyzed C−P Bond Activation DOI

Feng‐Ping Zhang,

Rong‐Hua Wang,

Jiang‐Fei Li

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(49)

Published: Oct. 17, 2023

Intermolecular carbophosphination reaction of alkynes or alkenes with unreactive C-P bonds remains an elusive challenge. Herein, we used a Ni-Al bimetallic catalyst to realize intermolecular 5-membered phosphole oxides, providing series 7-membered phosphepines in up 94 % yield.

Language: Английский

Citations

6
Computational Exploration of 1,2-Carboamine Carbonylation Catalyzed by Nickel DOI

Yi-Wen Gu,

Man Chen, Wei Deng

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(7), P. 4484 - 4495

Published: March 12, 2024

Nickel-catalyzed carbonylation of alkenes is a stereoselective and regioselective method for the synthesis amide compounds. Theoretical predictions with density functional theory calculations revealed mechanism origin stereoselectivity regioselectivity nickel-catalyzed norbornene. The reaction proceeds through oxidative addition, migration insertion alkenes, subsequent reduction elimination to afford cis-carbonylation product. C–N bond activation amides unfavorable because addition ability C–C stronger than that bond. determining step migratory strained olefin. structural analysis shows steroselectivity controlled by steric hindrance methyl groups olefins substituents IMes in ligands.

Language: Английский

Citations

1
Enantioselective Carbonylative Cyclization of Alkenes with C–H Bonds for Synthesis of γ-Lactams Bearing an α-Quaternary Carbon DOI
Weiwei Xu, Yanan Sun,

Yuqing Jiang

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 19, 2024

The development of effective synthetic methods to construct γ-lactams bearing a chiral α-quaternary carbon from relatively inert C(O)–H bonds with alkenes has been an elusive challenge. Herein, we used naphthylamine-derived phosphine oxide ligating Ni and Al bimetallic catalyst realize carbonylative cyclization formyl C–H alkenes, highly regio- enantioselectively constructing in up 99% yield 98% ee. These proved be versatile precursors for many biologically active molecules.

Language: Английский

Citations

1