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Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

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In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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Radical Substitution: Allylic Chlorination01:31

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Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
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π Molecular Orbitals of the Allyl Cation and Anion01:18

π Molecular Orbitals of the Allyl Cation and Anion

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An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each with...
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Preparation of Amines: Alkylation of Ammonia and Amines01:30

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Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
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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.
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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.
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Late-Stage Intermolecular Allylic C-H Amination.

Takafumi Ide1, Kaibo Feng1, Charlie F Dixon1

  • 1Department of Chemistry, Roger Adams Laboratory, University of Illinois, 505 South Mathews Avenue, Urbana, Illinois 61801, United States.

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|September 13, 2021
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This study introduces a manganese catalyst for selective late-stage allylic amination of complex molecules. This breakthrough enables efficient nitrogen introduction into natural products, potentially altering their biological activity.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Natural Product Synthesis

Background:

  • Allylic C-H functionalization is key for modifying natural products.
  • Intermolecular allylic amination faces challenges in reactivity and selectivity, limiting substrate scope.

Purpose of the Study:

  • To develop a selective and efficient method for intermolecular allylic C-H amination.
  • To enable late-stage functionalization of diverse and complex organic molecules, including natural products.

Main Methods:

  • Utilized a sustainable manganese perchlorophthalocyanine catalyst ([MnIII(ClPc)]).
  • Investigated the amination of 32 cyclic and linear compounds, including those with competing functional groups.
  • Conducted mechanistic studies to understand catalyst selectivity.

Main Results:

  • Achieved selective, preparative intermolecular allylic C-H amination across a range of substrates.
  • Demonstrated high site-, regio-, and diastereoselectivity (>20:1) in late-stage functionalization of natural products.
  • Catalyst's electrophilic and bulky nature, along with a stepwise mechanism, contribute to selectivity.

Conclusions:

  • The [MnIII(ClPc)] catalyst offers a robust solution for challenging allylic amination reactions.
  • This method significantly advances late-stage functionalization strategies for natural products and complex molecules.
  • The catalyst's selectivity broadens the applicability of allylic amination in synthetic chemistry.