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Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.

Preparation of Amines: Reduction of Amides and Nitriles

Preparation of Amines: Reduction of Amides and Nitriles

Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

Amines to Alkenes: Hofmann Elimination

Amines to Alkenes: Hofmann Elimination

Alkenes can be obtained from amines via an E2 elimination. The amine is first converted into a good leaving group, such as a quaternary ammonium salt. This is accomplished by treating the amine with an excess of alkyl halide, which results in a halide salt. Next, the halide salt is transformed into a hydroxide salt that functions as a base to enable elimination.
Under thermal conditions, the hydroxide can abstract a proton from the β carbon; this generates an alkene with the simultaneous...

Preparation of Amines: Reduction of Oximes and Nitro Compounds

Preparation of Amines: Reduction of Oximes and Nitro Compounds

Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

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Photoredox-HAT Catalysis for Primary Amine α-C-H Alkylation: Mechanistic Insight with Transient Absorption

Mahima Sneha^1,2, Georgia L Thornton¹, Luke Lewis-Borrell¹

¹School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, U.K.

ACS Catalysis

|June 21, 2023

Summary

Azide ion (N₃^-) acts as a hydrogen-atom transfer (HAT) catalyst for C-H alkylation. A novel N₆^•- radical anion forms, regulating the active N₃^• concentration during the photoredox catalytic cycle.

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Area of Science:

Organic Chemistry
Photocatalysis
Reaction Mechanisms

Background:

Synergistic use of photoredox catalysts and hydrogen-atom transfer (HAT) cocatalysts enables C(sp³)-H bond functionalization.
Azide ion (N₃^-) is a recently identified HAT catalyst for α-C-H alkylation of primary alkylamines using dicyanoarene photocatalysts like 4CzIPN.

Purpose of the Study:

To elucidate the kinetic and mechanistic details of the photoredox catalytic cycle involving azide ion and 4CzIPN.
To investigate the role of azide ion as a HAT cocatalyst in C-H functionalization reactions.

Main Methods:

Time-resolved transient absorption spectroscopy (sub-picosecond to microsecond timescales).
Time-resolved infrared and UV-visible spectroscopy.
Electronic structure calculations.

Main Results:

Direct observation of electron transfer from N₃^- to photoexcited 4CzIPN, involving the S₁ excited state.
Formation of the N₆^•- radical anion via rapid association of the N₃^• radical with N₃^-.
N₃^• identified as the active HAT participant, with N₆^•- acting as a regulator of N₃^• concentration.

Conclusions:

The N₆^•- radical anion plays a crucial role in modulating the concentration of the active N₃^• radical.
This study provides key mechanistic insights into azide-mediated photoredox catalysis for C-H functionalization.