scholarly journals Nickel-Catalyzed Decarboxylative Coupling of Redox-Active Esters with Aliphatic Aldehydes

2021 ◽  
Author(s):  
Jichao Xiao ◽  
Zhenning Li ◽  
John Montgomery
Keyword(s):  
Catalytic Reactions ◽  
Reductive Coupling ◽  
Nickel Catalysis ◽  
Mechanistic Studies ◽  
Radical Chain ◽  
Aliphatic Aldehydes ◽  
Active Esters ◽  
Redox Active ◽  
Decarboxylative Coupling ◽  
Nucleophilic Reagents

The addition of alkyl fragments to aliphatic aldehydes is a highly desirable transformation for fragment couplings, yet existing methods come with operational challenges related to the basicity and instability of the nucleophilic reagents commonly employed. We report herein that nickel catalysis using a readily available bioxazoline (BiOx) ligand can catalyze the reductive coupling of redox-active esters with aliphatic aldehydes using zinc metal as the reducing agent to deliver silyl-protected secondary alcohols. This protocol is operationally simple, proceeds under mild conditions, and tolerates a variety of functional groups. Initial mechanistic studies suggest a radical chain pathway. Additionally, alkyl tosylates and epoxides are suitable alkyl precursors to this transformation providing a versatile suite of catalytic reactions for the functionalization of aliphatic aldehydes.

Visible-Light-Induced Copper-Catalyzed Decarboxylative Coupling of Redox-Active Esters with N-Heteroarenes

2019 ◽  
Vol 21 (14) ◽  
pp. 5728-5732 ◽  
Author(s):  
Xue-Li Lyu ◽  
Shi-Sheng Huang ◽  
Hong-Jian Song ◽  
Yu-Xiu Liu ◽  
Qing-Min Wang
Keyword(s):  
Visible Light ◽  
Active Esters ◽  
Redox Active ◽  
Decarboxylative Coupling

Visible-light induced decarboxylative coupling of redox-active esters with disulfides to construct C–S bonds

2020 ◽  
Vol 56 (30) ◽  
pp. 4164-4167 ◽  
Author(s):  
Zhiwei Xiao ◽  
Lu Wang ◽  
Junjie Wei ◽  
Chongzhao Ran ◽  
Steven H. Liang ◽  
...  
Keyword(s):  
Visible Light ◽  
Active Esters ◽  
Redox Active ◽  
Decarboxylative Coupling ◽  
Novel Method

A novel method has been established for the construction of C–S bonds using redox-active esters with disulfides in the presence of Ru-photoredox catalyst.

scholarly journals Reductive coupling of imines with redox-active esters by visible light photoredox organocatalysis

2020 ◽  
Vol 7 (3) ◽  
pp. 602-608 ◽  
Author(s):  
Jiaqi Jia ◽  
Quentin Lefebvre ◽  
Magnus Rueping
Keyword(s):  
Visible Light ◽  
Bioactive Molecules ◽  
Secondary Amines ◽  
Reductive Coupling ◽  
Active Esters ◽  
Redox Active

The direct alkylation of imines with redox-active esters by visible light photoorganocatalysis provides a direct way for accessing α-branched secondary amines which are found in numerous bioactive molecules.

Metal-free reductive coupling of aliphatic aldehydes/ketones with 4-cyanopyridines: expanded scope and mechanistic studies

2020 ◽  
Vol 7 (18) ◽  
pp. 2744-2751
Author(s):  
Liuzhou Gao ◽  
Guoqiang Wang ◽  
Hui Chen ◽  
Jia Cao ◽  
Xiaoshi Su ◽  
...  
Keyword(s):  
Reductive Coupling ◽  
Mechanistic Studies ◽  
Aliphatic Aldehydes ◽  
Metal Free ◽  
Wide Range ◽  
Convenient Route

A practical B2pin2 mediated reductive coupling of 4-cyanopyridine with aliphatic aldehydes/ketones has been established. This metal-free protocol provides a convenient route to construct a wide range of C4-pyridine-functionalized alcohols.

Mechanistic Study and Development of Catalytic Reactions of Sm(II)

2018 ◽  
Author(s):  
Sandepan Maity ◽  
Robert Flowers
Keyword(s):  
Molecular Weight ◽  
High Molecular Weight ◽  
Proton Donor ◽  
Catalytic Reactions ◽  
Mechanistic Study ◽  
Mechanistic Studies ◽  
Cyclization Reactions ◽  
Mechanistic Approach ◽  
Donor Source

Despite the broad utility and application of SmI<sub>2</sub>in synthesis, the reagent is used in stoichiometric amounts and has a high molecular weight, resulting in a large amount of material being used for reactions requiring one or more equivalents of electrons. We report mechanistic studies on catalytic reactions of Sm(II) employing a terminal magnesium reductant and trimethyl silyl chloride in concert with a non-coordinating proton donor source. Reactions using this approach permitted reductions with as little as 1 mol% Sm. The mechanistic approach enabled catalysis employing HMPA as a ligand, facilitating the development of catalytic Sm(II) 5-<i>exo</i>-<i>trig </i>ketyl olefin cyclization reactions.

Connecting Remote C–H Bond Functionalization and Decarboxylative Coupling Using Simple Amines

2019 ◽  
Author(s):  
Francisco de Azambuja ◽  
Ming-Hsiu Yang ◽  
Alexander Bruecker ◽  
Paul Cheong ◽  
Ryan Altman
Keyword(s):  
Organic Molecules ◽  
Mechanistic Studies ◽  
Bond Functionalization ◽  
Bond Forming ◽  
Decarboxylative Coupling

The manuscript describes a Pd-catalyzed reaction of benzylic electrophiles that gives para-substituted arene products. Mechanistic studies suggest a mechanism involving a dearomative C–C bond-forming step, followed by base-mediated rearomatization. This mechanism is uncommon and underappreciated in Pd-catalysis and further exploitation of this mechanism should enable access to other organic molecules.

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