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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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A method involving the transformation of methyl ketones to carboxylic acids using excess base and halogen is called the haloform reaction. It begins with the deprotonation of α hydrogen to form an enolate ion which reacts with the electrophilic halogen to give an α-halo ketone. The step continues until all the α protons are substituted to form a trihalomethyl ketone. The resulting molecule is unstable, and in the presence of a hydroxide base, it readily undergoes nucleophilic...
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In the presence of heat or light, alkanes react with molecular halogens to form alkyl halides by a substitution reaction called radical halogenation. This reaction has three steps: initiation, propagation, and termination, as seen in the radical chlorination of methane to produce methyl chloride.
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α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
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Cross- and Multi-Coupling Reactions Using Monofluoroalkanes.

Takanori Iwasaki1, Nobuaki Kambe2

  • 1Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-8656, Japan.

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This review explores selective carbon-carbon bond formation by cleaving stable carbon-fluorine bonds in monofluorinated compounds. It details methods like cross-coupling and multi-component reactions, advancing organic synthesis.

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C−F bond cleavageFriedel-Crafts reactionalkyl fluoridecross-coupling reactionmulti-component coupling reaction

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Organofluorine Chemistry

Background:

  • Carbon-fluorine (C-F) bonds are exceptionally stable, posing challenges for chemical transformations.
  • Selective manipulation of C-F bonds is crucial for developing novel synthetic methodologies in organic chemistry.

Purpose of the Study:

  • To review C-C bond formation strategies involving the cleavage of C-F bonds at monofluorinated sp³-hybridized carbons.
  • To discuss various C-F bond cleavage mechanisms and the utility of alkyl fluorides in coupling reactions.

Main Methods:

  • Focuses on cross-coupling and multi-component coupling reactions for C-C bond formation.
  • Categorizes C-F bond cleavage mechanisms into Lewis acid-promoted elimination, nucleophilic substitution, and single electron transfer.
  • Compares the reactivity of alkyl fluorides with other (pseudo)halides as electrophilic coupling partners.

Main Results:

  • Demonstrates that selective C-F bond cleavage is achievable under specific conditions.
  • Highlights three primary mechanisms for C-F bond cleavage at sp³-hybridized carbons.
  • Identifies alkyl fluorides as effective electrophilic counterparts in coupling reactions.

Conclusions:

  • Selective C-C bond formation via C-F bond cleavage offers valuable synthetic routes.
  • Understanding C-F bond cleavage mechanisms is key to designing efficient synthetic strategies.
  • Alkyl fluorides present unique advantages as coupling partners in organic synthesis.