Nickel(II)‐Catalyzed Hydrocarbamoylation of Alkynes with Formamides towards Unsaturated Amides DOI

Tian‐Gui Li,

Shiyang Wang,

Zongxiang Xia

et al.

Helvetica Chimica Acta, Journal Year: 2024, Volume and Issue: 107(8)

Published: June 3, 2024

Abstract Ni‐catalyzed activation of C(sp 2 )−H bond remains an elusive challenge. Herein, we realized a selective formamides, which underwent addition reaction with internal alkynes to provide α,β‐unsaturated amide compounds in high yields. The protocol was featured by the cheap and nontoxic catalyst system. Preliminary mechanistic studies shed light on pathways.

Language: Английский

Ligand-Controlled, Nickel-Catalyzed Stereodivergent Construction of 1,3-Nonadjacent Stereocenters DOI

Qi Pan,

Kuai Wang,

Weipeng Xu

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(22), P. 15453 - 15463

Published: May 25, 2024

In contrast to the asymmetric synthesis of molecules with a single stereocenter or 1,2-adjacent stereocenters, simultaneous construction acyclic 1,3-nonadjacent stereocenters via catalyst in an enantioselective and diastereoselective manner remains formidable challenge. Here, we demonstrate diastereodivergent through Ni-catalyzed reductive cyclization/cross-coupling alkene-tethered aryl bromides α-bromoamides, which represents major remaining stereochemical challenge cyclization/difunctionalization alkenes. Using Ming-Phos as ligand, diverse set oxindoles containing were obtained high levels enantio- diastereoselectivity. Mechanistic experiments density functional theory calculations indicate that magnesium salt plays key role controlling Furthermore, another complementary stereoisomeric products constructed from same starting materials using Ph-Phox ligand.

Language: Английский

Citations

12
Enantioselective Directed Nickel-Catalyzed Three-Component Reductive Arylalkylation of Alkenes via the Carbometalation/Radical Cross-Coupling Sequence DOI

Zhan Dong,

Changyu Xu,

Jianchao Chang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(7), P. 4395 - 4406

Published: March 8, 2024

Asymmetric reductive three-component arylalkylation of alkenes via the radical relay method has been well established, while asymmetric migratory insertion strategy remains unexplored. We report enantioselective nickel-catalyzed cross-electrophile with aryl- and alkyl halides an integrated Heck carbometalation/radical cross-coupling sequence. This protocol employing a chiral Ni/PHOX catalytic system allows terminal internal to successfully engage exquisite control regio-, chemo-, stereoselectivity. More importantly, this undergoes regio- arylnickelation followed by Csp3–Csp3 elimination, thus exhibiting reverse regioselectivity method. Mild reaction conditions exceptional functional group tolerance facilitate method's compatibility bioactive motifs modular synthesis biologically active compounds. The experiments density theory calculations provide insights into mechanism origin stereoselectivity, hemilabile nature PHOX ligand is critical for achieving arylalkylation.

Language: Английский

Citations

11
Silanes as a versatile hydride source for Ni–H catalysis: a promising tool for π-hydro functionalization DOI
Yafia Kousin Mirza, Partha Sarathi Bera, Sachin Balaso Mohite

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(15), P. 4290 - 4317

Published: Jan. 1, 2024

Nickel-catalyzed hydrofunctionalization of π-substrates is a possibly effective method to synthesize several value-added molecular architectures. This review covers the NiH catalyzed reactions alkenes, alkynes and allenes.

Language: Английский

Citations

6
Isolation and Reactivity of Arylnickel(II) Complexes in Nickel-Catalyzed Borylation of Aryl Fluorosulfates DOI Creative Commons
Manoj Kumar Sahoo, Jeong Woo Lee, Soochan Lee

et al.

JACS Au, Journal Year: 2024, Volume and Issue: 4(4), P. 1646 - 1653

Published: March 25, 2024

Aryl fluorosulfates have emerged as versatile SuFExable substrates, harnessing the reactivity of S-F bond. In this study, we unveil their alternative synthetic utility in nickel-catalyzed borylation via C-O bond activation. This method highlights mild reaction conditions, a broad substrate scope, and moderate functional group tolerance, rendering it practical appealing approach for synthesizing diverse array aryl boronate esters. Furthermore, computational analysis sheds light on pathways, uncovering participation LNi(0) LNi(II)ArX species. insight is supported by

Language: Английский

Citations

5
Synthesis of (Z)-Allylsilanes by Cu-Catalyzed Regioselective Protosilylation of Allenes via a Single-Electron Process DOI
Min Ho Kim, S. Kim,

Yurim Lee

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 2380 - 2388

Published: Jan. 25, 2025

Language: Английский

Citations

0
Ni/Photoredox-catalyzed coupling of aryl bromides and methylenecyclopropanes via selective distal bond cleavage DOI

Ben Mao,

Min Shi, Yin Wei

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(18), P. 5033 - 5043

Published: Jan. 1, 2024

A series of 1,1-dibenzylethylene derivatives were obtained in moderate-to-good yields via double coupling aryl bromides and methylenecyclopropanes Ni/photoredox catalysis. The critical roles nickel this reaction disclosed.

Language: Английский

Citations

2
Nickel-Catalyzed Regio- and Stereoselective Hydroalkylation of Allenes: Exploiting the Unique Reactivity of Diazo Compounds as an Alkylating Source DOI

Ujjwal Karmakar,

Jae‐Han Bae,

Jin A Kim

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(22), P. 16570 - 16576

Published: Oct. 25, 2024

The reactivity of allenes has historically been limited with no previous examples their hydroalkylation using diazo compounds in any transition-metal catalytic framework. In this study, we present a Ni-catalyzed regio- and stereoselective reaction utilizing as alkylating agents. success method can be attributed to the use pyridine-based P,N ligand, which combines advantages both phosphine nitrogen ligands. Additionally, carbonyl group compound facilitates formation stable intermediates. Our detailed mechanistic studies reveal that proceeds through an initial interaction compound, followed by engagement allene.

Language: Английский

Citations

2
Ni-catalyzed regioselective C–C bond formation of 1,1-disubstituted allenes with aldehydes DOI
Seoyeon Kim, Jin‐Young Kim,

Shrikant D. Tambe

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(3), P. 816 - 821

Published: Dec. 11, 2023

A regio- and stereoselective coupling process between allenes aldehydes has been developed to obtain a linear homoallylic secondary alcohols by photoredox/Ni dual catalysis.

Language: Английский

Citations

4
Nickel-Catalyzed Double Deoxygenative C–N Coupling of Acyloxyamines DOI

Kashif Ali,

Eun Jin Cho

Organic Letters, Journal Year: 2024, Volume and Issue: 26(24), P. 5192 - 5195

Published: June 10, 2024

A double deoxygenative C-N coupling protocol has been developed by employing acyloxyamines through N-O bond activation. The formation under mild reaction conditions, NiCl

Language: Английский

Citations

1
Charge-recombinative triplet sensitization of alkenes for DeMayo-type [2 + 2] cycloaddition DOI Creative Commons
Yunjeong Lee, Byung Hak Jhun,

Sihyun Woo

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(30), P. 12058 - 12066

Published: Jan. 1, 2024

This work revealed the occurrence of charge-recombinative triplet sensitization in DeMayo-type [2 + 2] cycloaddition reactions catalyzed by indole-fused organophotocatalysts.

Language: Английский

Citations

1