Visible-Light-Induced\nα‑Arylation of\nKetones with (Hetero)aryl Halides

An enamine-mediated photoredox catalyzed C(sp<sup>2</sup>)–C(sp<sup>3</sup>) cross-coupling of dual radical precursors\nfor the arylation\nof ketone is presented in this Letter. These reactions led to the\nformation of an enamine by using pyrrolidine to functionalize the\nC(sp<sup>3</sup>)–H bond in ketone substrates, which could\nbe smoothly converted to α-arylated ketones with inert aryl\nbromides and even aryl chlorides in moderate to good yields under\nmild reaction conditions. The photocatalytically induced C(sp<sup>2</sup>)–C(sp<sup>3</sup>) cross-coupling between unactivated\nnoncyclic ketones and aryl halides was achieved, and multiple carbonyl\nα-arylated backbones containing various natural products and\ndrug molecules were successfully constructed.

Publication Details

Journal
Figshare
Published
2024-10-23
DOI
https://doi.org/10.1021/acs.orglett.4c03510.s001
Primary Topic
Urban and spatial planning
Type
article
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article

Visible-Light-Induced\nα‑Arylation of\nKetones with (Hetero)aryl Halides

Figshare
Urban and spatial planning
article

Visible-Light-Induced\nα‑Arylation of\nKetones with (Hetero)aryl Halides

article en

Abstract

An enamine-mediated photoredox catalyzed C(sp<sup>2</sup>)–C(sp<sup>3</sup>) cross-coupling of dual radical precursors\nfor the arylation\nof ketone is presented in this Letter. These reactions led to the\nformation of an enamine by using pyrrolidine to functionalize the\nC(sp<sup>3</sup>)–H bond in ketone substrates, which could\nbe smoothly converted to α-arylated ketones with inert aryl\nbromides and even aryl chlorides in moderate to good yields under\nmild reaction conditions. The photocatalytically induced C(sp<sup>2</sup>)–C(sp<sup>3</sup>) cross-coupling between unactivated\nnoncyclic ketones and aryl halides was achieved, and multiple carbonyl\nα-arylated backbones containing various natural products and\ndrug molecules were successfully constructed.

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Urban and spatial planning
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