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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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Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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Introduction
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Rh-catalyzed tunable defluorinative borylation.

Fei Hao1, Xueyun Shang2, Zhenwei Liu2

  • 1Shandong Provincial Key Laboratory of Molecular Engineering, Qilu University of Technology-Shandong Academy of Science, Ji'nan 250353, China and Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China. zhanghe07@gmail.com jlin@sioc.ac.cn jchxiao@sioc.ac.cn.

Chemical Communications (Cambridge, England)
|June 28, 2021
PubMed
Summary
This summary is machine-generated.

This study introduces a Rh-catalyzed reaction for defluorinative borylation of allylic gem-difluorides. The process yields valuable allylborylated and homoallylborylated monofluoroalkenes with high selectivity, offering versatile synthetic pathways.

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Area of Science:

  • Organic Chemistry
  • Organometallic Chemistry
  • Fluorine Chemistry

Background:

  • Allylic gem-difluorides are versatile precursors in organic synthesis.
  • Developing selective methods for functionalizing fluorinated compounds remains a challenge.
  • Rhodium-catalyzed reactions offer unique reactivity for C-F bond activation.

Purpose of the Study:

  • To develop a novel Rh-catalyzed defluorinative borylation of allylic gem-difluorides.
  • To achieve tunable synthesis of allylborylated and homoallylborylated monofluoroalkenes.
  • To explore the synthetic utility of the obtained products.

Main Methods:

  • Rhodium-catalyzed defluorinative borylation using allylic gem-difluorides.
  • Optimization of reaction conditions to control reaction pathways and selectivity.
  • Subsequent conversion of borylated products to dihydroxyl-containing monofluoroalkenes.

Main Results:

  • Successful synthesis of allylborylated and homoallylborylated monofluoroalkenes with high Z/E selectivity.
  • Demonstration of distinct reaction pathways by subtle changes in reaction conditions.
  • Efficient transformation of allylborylated products into valuable dihydroxyl-containing monofluoroalkenes.

Conclusions:

  • The developed Rh-catalyzed method provides a powerful tool for synthesizing selectively functionalized monofluoroalkenes.
  • The reaction's tunable nature allows access to different product classes.
  • The study expands the synthetic utility of allylic gem-difluorides in organoboron chemistry.