4.8 Article

Nickel-Catalyzed Direct Substitution of Allylic Alcohols with Nitriles: A General Tool for the Construction of Acyclic C2-Tertiary or Quaternary Benzyl Nitriles

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
Article Chemistry, Physical

Catalytic Formal Conjugate Addition: Direct Synthesis of δ-Hydroxynitriles from Nitriles and Allylic Alcohols

Subramanian Thiyagarajan et al.

Summary: This article describes a simple method for the coupling of nitriles with allylic alcohols catalyzed by a ruthenium pincer complex. Mechanistic studies were conducted to investigate the catalytic cycle. The method demonstrated tolerability towards reactive functional groups such as carbamate, sulfonate, olefin, cyano, and trifluoromethyl-substituted benzyl nitriles. Additionally, the synthesis of anipamil drug and the utility of delta-hydroxynitrile products in the synthesis and functionalization of biologically active molecules were demonstrated.

ACS CATALYSIS (2022)

Review Chemistry, Multidisciplinary

Carbon-Carbon Bond Cleavage at Allylic Positions: Retro-allylation and Deallylation

Keisuke Nogi et al.

Summary: The retroallylation and deallylation of allylic compounds are intriguing methods for cleavage of C-C sigma bonds, generating valuable allylic metal compounds and serving as protective groups for acidic C-H bonds. These transformations offer wide application in regio-, stereo-, and enantioselective synthesis.

CHEMICAL REVIEWS (2021)

Article Chemistry, Applied

Efficient and Clean Nickel Catalyzed α-Allylation Reaction of Nitriles

Bouchaib Mouhsine et al.

Summary: A clean method has been developed for the a-allylation of phenyl and alpha alkyl phenyl acetonitrile with allylic alcohols, catalyzed by nickel complexes in situ at 80 degrees C in methanol. The protocol, which only yields water as a side-product, can synthesize many allylic nitriles with good yields.

ADVANCED SYNTHESIS & CATALYSIS (2021)

Article Chemistry, Organic

Nickel-Catalyzed C(sp3)-H Functionalization of Benzyl Nitriles: Direct Michael Addition to Terminal Vinyl Ketones

Ninghui Zhang et al.

Summary: An efficient nickel-catalyzed addition of benzyl nitriles to terminal vinyl ketones via C(sp(3))-H functionalization has been developed, providing a novel protocol for the synthesis of α-functionalized benzyl nitriles with structural diversity under mild reaction conditions without the use of a strong base. This work might be potentially useful towards the development of an enantioselective variant using chiral nitrogen ligands.

ORGANIC LETTERS (2021)

Review Chemistry, Organic

Advances in Deallylation

Yu Wang et al.

Summary: Allyl groups serve as versatile protective groups in organic synthesis, being stable under various conditions and easily removed under mild conditions. They play a significant role in the synthesis of natural products and pharmaceutical industry. Various methods of deallylation have been developed in recent decades.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

The salt-free nickel-catalysed α-allylation reaction of ketones with allyl alcohol and diallylether

Bouchaib Mouhsine et al.

GREEN CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Nickel-Catalyzed Direct Coupling of Allylic Alcohols with Organoboron Reagents

Gaonan Wang et al.

CHINESE JOURNAL OF CHEMISTRY (2018)

Article Chemistry, Multidisciplinary

Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols

Aurapat Ngamnithiporn et al.

CHEMICAL SCIENCE (2018)

Article Chemistry, Organic

Synthesis of Chiral Homoallylic Nitriles by Iridium-Catalyzed Allylation of Cyanoacetates

Asuka Matsunami et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

Article Chemistry, Multidisciplinary

Nickel-Catalyzed α-Allylation of Aldehydes and Tandem Aldol Condensation/Allylation Reaction with Allylic Alcohols

Yann Bernhard et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Asymmetric Allylic Alkylation of -Ketoesters with Allylic Alcohols by a Nickel/Diphosphine Catalyst

Yusuke Kita et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Nickel-Catalyzed Allylic Alkylation with Diarylmethane Pronucleophiles: Reaction Development and Mechanistic Insights

Sheng-Chun Sha et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Organic

Nickel-Catalysed Bis-Allylation of Activated Nucleophiles with Allyl Alcohol

Remi Blieck et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2016)

Review Chemistry, Multidisciplinary

Transition metal-catalyzed allylic substitution reactions with unactivated allylic substrates

Nicholas A. Butt et al.

CHEMICAL SOCIETY REVIEWS (2015)

Article Chemistry, Multidisciplinary

Enantioselective Rhodium-Catalyzed Allylic Substitution with a Nitrile Anion: Construction of Acyclic Quaternary Carbon Stereogenic Centers

Ben W. H. Turnbull et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Organic

Catalytic α-Monoallylation of Aryl Acetonitriles

Tapan Maji et al.

ORGANIC LETTERS (2014)

Review Chemistry, Multidisciplinary

Transition metal catalyzed nucleophilic allylic substitution: activation of allylic alcohols via pi-allylic species

Basker Sundararaju et al.

CHEMICAL SOCIETY REVIEWS (2012)

Article Chemistry, Multidisciplinary

Deacylative Allylation: Allylic Alkylation via Retro-Claisen Activation

Alexander J. Grenning et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

Review Chemistry, Multidisciplinary

Metal-catalyzed enantioselective allylation in asymmetric synthesis

Zhan Lu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)