scholarly journals Enamine/Transition Metal Combined Catalysis: Catalytic Transformations Involving Organometallic Electrophilic Intermediates

2019 ◽  
Vol 377 (6) ◽  
Author(s):  
Samson Afewerki ◽  
Armando Córdova
Keyword(s):  
Transition Metal ◽  
Metal Complex ◽  
Carbonyl Compounds ◽  
Transition Metal Catalysis ◽  
Chemical Transformations ◽  
Considerable Effort ◽  
Metal Catalysis ◽  
First Report ◽  
Wide Range ◽  
Selective Chemical

AbstractThe concept of merging enamine activation catalysis with transition metal catalysis is an important strategy, which allows for selective chemical transformations not accessible without this combination. The amine catalyst activates the carbonyl compounds through the formation of a reactive nucleophilic enamine intermediate and, in parallel, the transition metal activates a wide range of functionalities such as allylic substrates through the formation of reactive electrophilic π-allyl-metal complex. Since the first report of this strategy in 2006, considerable effort has been devoted to the successful advancement of this technology. In this chapter, these findings are highlighted and discussed.

Recent Progress in Radical Decarboxylative Functionalizations Enabled by Transition-Metal (Ni, Cu, Fe, Co or Cr) Catalysis

Synthesis ◽  
2020 ◽  
Vol 53 (01) ◽  
pp. 1-29
Author(s):  
Yahu A Liu ◽  
Xuebin Liao ◽  
Hui Chen
Keyword(s):  
Transition Metal ◽  
Carboxylic Acids ◽  
Recent Progress ◽  
Bond Formation ◽  
Transition Metal Catalysis ◽  
Great Success ◽  
Chemical Transformations ◽  
Metal Catalysis ◽  
Redox Active ◽  
Aliphatic Carboxylic Acids

AbstractAliphatic carboxylic acids are abundant in natural and synthetic sources and are widely used as connection points in many chemical transformations. Radical decarboxylative functionalization promoted by transition-metal catalysis has achieved great success, enabling carboxylic acids to be easily transformed into a wide variety of products. Herein, we highlight the recent advances made on transition-metal (Ni, Cu, Fe, Co or Cr) catalyzed C–X (X = C, N, H, O, B, or Si) bond formation as well as syntheses of ketones, amino acids, alcohols, ethers and difluoromethyl derivatives via radical decarboxylation of carboxylic acids or their derivatives, including, among others, redox-active esters (RAEs), anhydrides, and diacyl peroxides.1 Introduction2 Ni-Catalyzed Decarboxylative Functionalizations3 Cu-Catalyzed Decarboxylative Functionalizations4 Fe-Catalyzed Decarboxylative Functionalizations5 Co- and Cr-Catalyzed Decarboxylative Functionalizations6 Conclusions

Transition Metal-Catalyzed Enantioselective α-Arylation of Carbonyl Compounds to Give Tertiary Stereocenters

Synthesis ◽  
2021 ◽  
Author(s):  
Manuel Orlandi ◽  
Margarita Escudero-Casao ◽  
Giulia Licini
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Carbonyl Group ◽  
Carbonyl Compounds ◽  
Short Review ◽  
Transition Metal Catalysis ◽  
Biologically Active ◽  
Metal Catalysis ◽  
Quaternary Stereocenters ◽  
Metal Catalyzed

Enantioenriched α-aryl carbonyl compounds are ubiquitous in natural products and biologically active compounds. Their synthesis has been explored over the last few decades and several methods now exist that allow for the enantioselective formation of a C(sp3)-C(sp2) bond in α-position to a carbonyl group. However, although the formation of quaternary stereocenters has been fairly well established, the enantioselective formation of tertiary stereocenters proved more challenging due to facile product post-reaction racemization. In this short review, we summarize the methods reported so far for the asymmetric α-arylation of enolates and analogues that rely on transition metal catalysis.

Carbon‐Sulfur Bond Constructions: From Transition‐Metal Catalysis to Sustainable Catalysis

2021 ◽  
Author(s):  
Pratheepkumar Annamalai ◽  
Ke‐Chien Liu ◽  
Satpal Singh Badsara ◽  
Chin‐Fa Lee
Keyword(s):  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Sulfur Bond

An electrochemical perspective on the roles of ligands in the merger of transition-metal catalysis and electrochemistry

2020 ◽  
Author(s):  
Ke-Yin Ye ◽  
Jun-Song Zhong ◽  
Yi Yu ◽  
Zhaojiang Shi
Keyword(s):  
Transition Metal ◽  
Organic Synthesis ◽  
Transition Metal Catalysis ◽  
Metal Catalysis

The merger of transition-metal catalysis and electrochemistry has been emerging as a very versatile and robust synthetic tool in organic synthesis. Like in their non-electrochemical variants, ligands also play crucial...

Insertion Reaction of 2-Halo-N-allylanilines with K2S Involving Trisulfur Radical Anion: Synthesis of Benzothiazole Derivatives under Transition-Metal-Free Conditions

Synthesis ◽  
2020 ◽  
Author(s):  
Yan-Wei Zhao ◽  
Shun-Yi Wang ◽  
Xin-Yu Liu ◽  
Tian Jiang ◽  
Weidong Rao
Keyword(s):  
Transition Metal ◽  
Radical Anion ◽  
Radical Cyclization ◽  
Transition Metal Catalysis ◽  
Insertion Reaction ◽  
Metal Catalysis ◽  
Metal Free ◽  
Benzothiazole Derivatives

AbstractA synthesis of benzothiazole derivatives through the reaction of 2-halo-N-allylanilines with K2S in DMF is developed. The trisulfur radical anion S3·–, which is generated in situ from K2S in DMF, initiates the reaction without transition-metal catalysis or other additives. In addition, two C–S bonds are formed and heteroaromatization of benzothiazole is triggered by radical cyclization and H-shift.

scholarly journals Tandem rhodium catalysis: exploiting sulfoxides for asymmetric transition-metal catalysis

2015 ◽  
Vol 13 (21) ◽  
pp. 5844-5847 ◽  
Author(s):  
K. G. M. Kou ◽  
V. M. Dong
Keyword(s):  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Rhodium Catalysis ◽  
Alkene Hydrogenation

Sulfoxides are uncommon substrates for transition-metal catalysis due to their propensity to inhibit catalyst turnover. We have developed the first DKR of racemic allylic sulfoxides where rhodium catalyzed both sulfoxide epimerization and alkene hydrogenation.

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