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Related Concept Videos

Coupled Reactions01:17

Coupled Reactions

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Cellular processes such as building and breaking down complex molecules occur through stepwise chemical reactions. Some of these chemical reactions are spontaneous and release energy, whereas others require energy to proceed. Cells often couple the energy-releasing reaction with the energy-requiring one to carry out important cell functions. 
Energy in adenosine triphosphate or ATP molecules is easily accessible to do work. ATP powers the majority of energy-requiring cellular reactions....
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Crossed Aldol Reactions: Overview01:04

Crossed Aldol Reactions: Overview

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Crossed aldol addition is the reaction between two different carbonyl compounds under acidic or basic conditions. Here, both the carbonyl compounds function as nucleophiles and electrophiles. As shown in Figure 1, such a reaction yields a mixture of products, two of which are formed via self-condensation, while the remaining two are formed via crossed-condensation. Without adjustment, the reaction's usefulness in organic chemistry is decreased.
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Crossed Aldol Reaction Using Weak Bases01:14

Crossed Aldol Reaction Using Weak Bases

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This lesson deals with the crossed aldol reaction using weak bases. The self-condensation of an aldehyde having α hydrogen is prevented by adding it slowly to a mixture of formaldehyde and weak bases like hydroxide and alkoxide. Upon slow addition of the aldehyde, the base deprotonates the α carbon of the aldehyde to form the corresponding enolate. The enolate subsequently attacks the formaldehyde to form a single crossed product. Figure 1 depicts the aforementioned reaction.
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Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction00:56

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The reaction between two different carbonyl compounds comprising α hydrogen in the presence of a strong base like lithium diisopropylamide (LDA) to form a crossed aldol product is known as a directed aldol reaction. The directed aldol reaction is depicted in Figure 1.
2.8K
Preparation of Amides01:29

Preparation of Amides

4.0K
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
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Crossing Over01:34

Crossing Over

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Unlike mitosis, meiosis aims for genetic diversity in its creation of haploid gametes. Dividing germ cells first begin this process in prophase I, where each chromosome—replicated in S phase—is now composed of two sister chromatids (identical copies) joined centrally.
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Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
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Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents

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N-Boc-Amides in Cross-Coupling Reactions.

Yann Bourne-Branchu1, Corinne Gosmini1, Grégory Danoun1

  • 1LCM, CNRS, Ecole Polytechnique, Université Paris-Saclay, 91128, Palaiseau Cedex, France.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|October 13, 2018
PubMed
Summary

N-Boc-amides are increasingly used as electrophilic partners in cross-coupling reactions. This review highlights their synthetic utility and recent advancements in these important chemical transformations.

Keywords:
Boc activationC−N activationamidescross-couplinghomogeneous catalysis

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Amides are increasingly utilized as electrophilic partners in cross-coupling reactions since 2015.
  • N-Boc-amides demonstrate significant activity and synthetic utility in these transformations.

Purpose of the Study:

  • To review recent developments in cross-coupling reactions involving N-Boc-amides.
  • To highlight the synthetic usefulness of N-Boc-amides in organic synthesis.

Main Methods:

  • Literature review of recent advancements in cross-coupling reactions.
  • Analysis of the reactivity and applications of N-Boc-amides.

Main Results:

  • N-Boc-amides have emerged as versatile electrophilic partners.
  • Significant growth in the application of amides, particularly N-Boc-amides, in cross-coupling reactions.

Conclusions:

  • N-Boc-amides offer important synthetic advantages.
  • The field of amide-based cross-coupling reactions is rapidly evolving, with N-Boc-amides playing a key role.