B/Pd Synergistic Catalysis\nfor the Decarboxylative\nAllylation of 2‑(2-Azaaryl)acetic Acids

We\ndescribe an allylation reaction between 2-(2-azaaryl)acetic\nacids and allylic electrophiles catalyzed synergistically by a dual\nsystem consisting of borinic acid and a Pd complex under mild conditions.\nThe decarboxylative allylation proceeds via a boron-bound enamine\nintermediate, which then interacts with a π-allylpalladium intermediate\nfrom the allylic electrophile. High yields of diallylation products\nhighlight the method’s efficiency. Intriguingly, when using\n2-(2-pyridyl)acetic acid with a C3 substituent on the pyridyl ring,\nthe reaction exclusively yields monoallylation products.

Publication Details

Journal
Figshare
Published
2024-09-13
DOI
https://doi.org/10.1021/acs.joc.4c01634.s001
Primary Topic
Organoboron and organosilicon chemistry
Type
article
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article

B/Pd Synergistic Catalysis\nfor the Decarboxylative\nAllylation of 2‑(2-Azaaryl)acetic Acids

Figshare
Organoboron and organosilicon chemistry
article

B/Pd Synergistic Catalysis\nfor the Decarboxylative\nAllylation of 2‑(2-Azaaryl)acetic Acids

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Abstract

We\ndescribe an allylation reaction between 2-(2-azaaryl)acetic\nacids and allylic electrophiles catalyzed synergistically by a dual\nsystem consisting of borinic acid and a Pd complex under mild conditions.\nThe decarboxylative allylation proceeds via a boron-bound enamine\nintermediate, which then interacts with a π-allylpalladium intermediate\nfrom the allylic electrophile. High yields of diallylation products\nhighlight the method’s efficiency. Intriguingly, when using\n2-(2-pyridyl)acetic acid with a C3 substituent on the pyridyl ring,\nthe reaction exclusively yields monoallylation products.

Figshare
Openalex Percentile: Top 80%
Organoboron and organosilicon chemistry
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B/Pd Synergistic Catalysis\nfor the Decarboxylative\nAllylation of 2‑(2-Azaaryl)acetic Acids · Figshare (2024) | TGRS Research Map | TGRS