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Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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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.
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Amines to Amides: Acylation of Amines01:19

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Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

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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.
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Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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Amine-boranes bearing borane-incompatible functionalities: application to selective amine protection and surface

P Veeraraghavan Ramachandran1, Ameya S Kulkarni1, Yan Zhao1

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A new, scalable open-flask synthesis method for amine-boranes using common reagents is presented. This method tolerates diverse functional groups and yields stable molecules for applications like surface functionalization.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Surface Chemistry

Background:

  • Amine-boranes are versatile compounds with applications in synthesis and materials science.
  • Existing synthesis methods often require harsh conditions or specialized reagents.
  • Developing efficient and general methods for amine-borane synthesis is crucial.

Purpose of the Study:

  • To develop a general, cost-effective, and scalable open-flask synthesis for amine-boranes.
  • To demonstrate the compatibility of the synthesis with various amine functionalities.
  • To explore the utility of the synthesized amine-boranes in surface functionalization.

Main Methods:

  • Utilized inexpensive and readily available reagents: sodium borohydride, sodium bicarbonate, water, and amines.
  • Employed an open-flask reaction setup for synthesis.
  • Characterized the resulting amine-boranes and their stability.
  • Demonstrated surface functionalization using self-assembled layers.

Main Results:

  • Achieved the first general open-flask synthesis of amine-boranes.
  • Successfully synthesized amine-boranes with diverse, including borane-reactive, functional groups (alkene, alkyne, hydroxyl, thiol, ester, amide, nitrile, nitro).
  • Obtained stable amine-borane molecules with proximate electrophilic and nucleophilic centers.
  • Formed self-assembled monolayers of amine-boranes on gold (thiol-bearing) and silica (alkoxysilane-bearing) surfaces.

Conclusions:

  • A convenient, scalable, and versatile synthesis for amine-boranes has been established.
  • The synthesized amine-boranes represent a novel class of organic ligands.
  • This method enables facile surface functionalization of various materials.