TMSCN-Promoted Difunctionalization\nof Alkenes for\nthe Synthesis of Alcohol Derivatives

A TMSCN-promoted\ndifunctionalization of styrenes with CHCl<sub>3</sub> and TBHP is\nreported via the radical addition/cross coupling\nprocess. A wide range of dichloromethyl<i>-</i>substituted\nalcohol derivatives were synthesized under transition-metal-free conditions.\nBesides, this method is also applicable to unactive alkenes. The key\nto this success lies in the role of TMSCN, which prevents the reaction\ntoward dichloromethylperoxylation of olefins. This represents an alternative\napproach for synthesizing diverse alcohol derivatives using readily\navailable substrates, holding significant promise in the fields of\npharmaceutical chemistry and natural product synthesis.

Publication Details

Journal
Figshare
Published
2024-08-15
DOI
https://doi.org/10.1021/acs.joc.4c00870.s001
Primary Topic
Catalytic C–H Functionalization Methods
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article
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article

TMSCN-Promoted Difunctionalization\nof Alkenes for\nthe Synthesis of Alcohol Derivatives

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Catalytic C–H Functionalization Methods
article

TMSCN-Promoted Difunctionalization\nof Alkenes for\nthe Synthesis of Alcohol Derivatives

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Abstract

A TMSCN-promoted\ndifunctionalization of styrenes with CHCl<sub>3</sub> and TBHP is\nreported via the radical addition/cross coupling\nprocess. A wide range of dichloromethyl<i>-</i>substituted\nalcohol derivatives were synthesized under transition-metal-free conditions.\nBesides, this method is also applicable to unactive alkenes. The key\nto this success lies in the role of TMSCN, which prevents the reaction\ntoward dichloromethylperoxylation of olefins. This represents an alternative\napproach for synthesizing diverse alcohol derivatives using readily\navailable substrates, holding significant promise in the fields of\npharmaceutical chemistry and natural product synthesis.

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Catalytic C–H Functionalization Methods
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TMSCN-Promoted Difunctionalization\nof Alkenes for\nthe Synthesis of Alcohol Derivatives · Figshare (2024) | TGRS Research Map | TGRS