Rhodaelectro-Catalyzed\nSynthesis of Pyrano[3,4‑<i>b</i>]indol-1(9<i>H</i>)‑ones via the Double\nDehydrogenative Heck Reaction between Indole-2-carboxylic Acids and\nAlkenes

A rhodaelectro-catalyzed double dehydrogenative Heck\nreaction of\nindole-2-carboxylic acids with alkenes has been developed for the\nsynthesis of pyrano[3,4-<i>b</i>]indol-1(9<i>H</i>)-ones. The weakly coordinating carboxyl group is utilized twice\nas a directing group to activate the C–H bonds throughout the\nreaction. This reaction precedes an acceptorless dehydrogenation under\nexogenous oxidant-free conditions in an undivided cell with a constant\ncurrent.

Publication Details

Journal
Figshare
Published
2024-11-12
DOI
https://doi.org/10.1021/acs.joc.4c02271.s001
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Rhodaelectro-Catalyzed\nSynthesis of Pyrano[3,4‑b]indol-1(9H)‑ones via the Double\nDehydrogenative Heck Reaction between Indole-2-carboxylic Acids and\nAlkenes

Figshare
Catalytic C–H Functionalization Methods
article

Rhodaelectro-Catalyzed\nSynthesis of Pyrano[3,4‑b]indol-1(9H)‑ones via the Double\nDehydrogenative Heck Reaction between Indole-2-carboxylic Acids and\nAlkenes

article en

Abstract

A rhodaelectro-catalyzed double dehydrogenative Heck\nreaction of\nindole-2-carboxylic acids with alkenes has been developed for the\nsynthesis of pyrano[3,4-<i>b</i>]indol-1(9<i>H</i>)-ones. The weakly coordinating carboxyl group is utilized twice\nas a directing group to activate the C–H bonds throughout the\nreaction. This reaction precedes an acceptorless dehydrogenation under\nexogenous oxidant-free conditions in an undivided cell with a constant\ncurrent.

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Catalytic C–H Functionalization Methods
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Rhodaelectro-Catalyzed\nSynthesis of Pyrano[3,4‑<i>b</i>]indol-1(9<i>H</i>)‑ones via the Double\nDehydrogenative Heck Reaction between Indole-2-carboxylic Acids and\nAlkenes · Figshare (2024) | TGRS Research Map | TGRS