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Literature DB >> 35462625

Three-Component Ni-Catalyzed Silylacylation of Alkenes.

Abstract

A Ni-catalyzed silylacylation of alkenes is presented. The reaction combines alkenes, ClZnSiR3, and acid chlorides to provide rapid access to β-silyl ketones. Importantly, the method involves a [Ni]-SiR3 complex as a catalytic intermediate, which is rarely described for three-component alkene functionalization. Finally, the synthetic utility of the products is demonstrated, and the mechanistic details are described.

Entities: Chemical

Keywords: acylation; alkene; nickel; silylation; zinc

Year: 2021 PMID： 35462625 PMCID： PMC9031101 DOI： 10.1021/acscatal.0c05449

Source DB: PubMed Journal: ACS Catal Impact factor: 13.700

41 in total

1. Transition-Metal-Catalyzed 1,2-Carboboration of Alkenes: Strategies, Mechanisms, and Stereocontrol.

Authors: Zhen Liu; Yang Gao; Tian Zeng; Keary M Engle
Journal: Isr J Chem Date: 2019-09-10 Impact factor: 3.333

2. Ni-Catalyzed Alkene Carboacylation via Amide C-N Bond Activation.

Authors: James A Walker; Kevin L Vickerman; Jenna N Humke; Levi M Stanley
Journal: J Am Chem Soc Date: 2017-07-20 Impact factor: 15.419

3. Nickel-Catalyzed α-Carbonylalkylarylation of Vinylarenes: Expedient Access to γ,γ-Diarylcarbonyl and Aryltetralone Derivatives.

Authors: Shekhar Kc; Roshan K Dhungana; Namrata Khanal; Ramesh Giri
Journal: Angew Chem Int Ed Engl Date: 2020-03-19 Impact factor: 15.336

4. Silicon-Carbon Bond Formation via Nickel-Catalyzed Cross-Coupling of Silicon Nucleophiles with Unactivated Secondary and Tertiary Alkyl Electrophiles.

Authors: Crystal K Chu; Yufan Liang; Gregory C Fu
Journal: J Am Chem Soc Date: 2016-05-17 Impact factor: 15.419

5. Strategies toward Dicarbofunctionalization of Unactivated Olefins by Combined Heck Carbometalation and Cross-Coupling.

Authors: Ramesh Giri; Shekhar Kc
Journal: J Org Chem Date: 2018-03-05 Impact factor: 4.354

6. Ni(I)-Catalyzed β,δ-Vinylarylation of γ,δ-Alkenyl α-Cyanocarboxylic Esters via Contraction of Transient Nickellacycles.

Authors: Roshan K Dhungana; Shekhar Kc; Prakash Basnet; Vivek Aryal; Lucas J Chesley; Ramesh Giri
Journal: ACS Catal Date: 2019-10-29 Impact factor: 13.700

Three-Component Ni-Catalyzed Silylacylation of Alkenes.

1. Transition-Metal-Catalyzed 1,2-Carboboration of Alkenes: Strategies, Mechanisms, and Stereocontrol.

2. Ni-Catalyzed Alkene Carboacylation via Amide C-N Bond Activation.

3. Nickel-Catalyzed α-Carbonylalkylarylation of Vinylarenes: Expedient Access to γ,γ-Diarylcarbonyl and Aryltetralone Derivatives.

4. Silicon-Carbon Bond Formation via Nickel-Catalyzed Cross-Coupling of Silicon Nucleophiles with Unactivated Secondary and Tertiary Alkyl Electrophiles.

5. Strategies toward Dicarbofunctionalization of Unactivated Olefins by Combined Heck Carbometalation and Cross-Coupling.

6. Ni(I)-Catalyzed β,δ-Vinylarylation of γ,δ-Alkenyl α-Cyanocarboxylic Esters via Contraction of Transient Nickellacycles.

7. Nickel-Catalyzed Asymmetric Reductive Diarylation of Vinylarenes.

8. Directed nickel-catalyzed 1,2-dialkylation of alkenyl carbonyl compounds.

9. Ni-catalyzed 1,2-benzylboration of 1,2-disubstituted unactivated alkenes.

1. Directed, nickel-catalyzed 1,2-alkylsulfenylation of alkenyl carbonyl compounds.

2. Intermolecular Carbosilylation of α-Olefins with C(sp³ )-C(sp) Bond Formation Involving Silylium-Ion Regeneration.