Synthesis of C(3) SCF<sub>3</sub>‑Substituted\nPyrrolidinoindoline by P<sup>III</sup>/P<sup>V</sup> Redox Catalysis\nUsing CF<sub>3</sub>SO<sub>2</sub>Cl as Electrophilic CF<sub>3</

This work reports a method for the\ncatalytic synthesis of C(3)\nSCF<sub>3</sub>-substituted pyrrolidinindoline using a small-ring\norganophosphorus-based catalyst and a hydrosilane reductant, with\ntrifluoromethanesulfonyl chloride as the electrophilic SCF<sub>3</sub> reagent. This method can drive the conversion of tryptamine to the\nC(3) SCF<sub>3</sub>-substituted pyrrolidine indoline. The readily\navailable, inexpensive trifluoromethanesulfonyl chloride could be\nactivated as an electrophilic SCF<sub>3</sub> source by P<sup>III</sup>/P<sup>V</sup> redox catalysis and could efficiently participate\nin the reaction of tryptamines, thus providing various substituted\nC(3) SCF<sub>3</sub>-substituted pyrrolidinoindoline in moderate to\nexcellent yields. This presented strategy features a broad substrate\nscope, and the structure has value for in-depth research.

Publication Details

Journal
Figshare
Published
2024-08-04
DOI
https://doi.org/10.1021/acs.joc.4c01276.s001
Primary Topic
Mycorrhizal Fungi and Plant Interactions
Type
article
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article

Synthesis of C(3) SCF3‑Substituted\nPyrrolidinoindoline by PIII/PV Redox Catalysis\nUsing CF3SO2Cl as Electrophilic CF3</

Figshare
Mycorrhizal Fungi and Plant Interactions
article

Synthesis of C(3) SCF3‑Substituted\nPyrrolidinoindoline by PIII/PV Redox Catalysis\nUsing CF3SO2Cl as Electrophilic CF3</

article en

Abstract

This work reports a method for the\ncatalytic synthesis of C(3)\nSCF&lt;sub&gt;3&lt;/sub&gt;-substituted pyrrolidinindoline using a small-ring\norganophosphorus-based catalyst and a hydrosilane reductant, with\ntrifluoromethanesulfonyl chloride as the electrophilic SCF&lt;sub&gt;3&lt;/sub&gt; reagent. This method can drive the conversion of tryptamine to the\nC(3) SCF&lt;sub&gt;3&lt;/sub&gt;-substituted pyrrolidine indoline. The readily\navailable, inexpensive trifluoromethanesulfonyl chloride could be\nactivated as an electrophilic SCF&lt;sub&gt;3&lt;/sub&gt; source by P&lt;sup&gt;III&lt;/sup&gt;/P&lt;sup&gt;V&lt;/sup&gt; redox catalysis and could efficiently participate\nin the reaction of tryptamines, thus providing various substituted\nC(3) SCF&lt;sub&gt;3&lt;/sub&gt;-substituted pyrrolidinoindoline in moderate to\nexcellent yields. This presented strategy features a broad substrate\nscope, and the structure has value for in-depth research.

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Mycorrhizal Fungi and Plant Interactions
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Synthesis of C(3) SCF&lt;sub&gt;3&lt;/sub&gt;‑Substituted\nPyrrolidinoindoline by P&lt;sup&gt;III&lt;/sup&gt;/P&lt;sup&gt;V&lt;/sup&gt; Redox Catalysis\nUsing CF&lt;sub&gt;3&lt;/sub&gt;SO&lt;sub&gt;2&lt;/sub&gt;Cl as Electrophilic CF&lt;sub&gt;3&lt;/ · Figshare (2024) | TGRS Research Map | TGRS