Bifunctional\nLewis Base-Catalyzed (3 + 2) Cycloadditions\nof Pyrazolone-Derived MBH Carbonates with Arynes

The (3 + 2) cycloaddition of arynes with allylic ylides\nremains\na formidable challenge because both intermediates are highly reactive\nand prone to spontaneous quenching. Here, we report a (3 + 2) cycloaddition\nof pyrazolone MBH carbonates with arynes, enabling the efficient synthesis\nof diverse indene-fused spiropyrazolones. The key is employing a new\nbifunctional Lewis base catalyst to facilitate the cycloaddition of <i>in situ</i> generated allylic pyridinium ylides with arynes.

Publication Details

Journal
Figshare
Published
2024-10-16
DOI
https://doi.org/10.1021/acs.orglett.4c03410.s001
Primary Topic
Cyclization and Aryne Chemistry
Type
article
Field-Weighted Citation Impact
0.00
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article

Bifunctional\nLewis Base-Catalyzed (3 + 2) Cycloadditions\nof Pyrazolone-Derived MBH Carbonates with Arynes

Figshare
Cyclization and Aryne Chemistry
article

Bifunctional\nLewis Base-Catalyzed (3 + 2) Cycloadditions\nof Pyrazolone-Derived MBH Carbonates with Arynes

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Abstract

The (3 + 2) cycloaddition of arynes with allylic ylides\nremains\na formidable challenge because both intermediates are highly reactive\nand prone to spontaneous quenching. Here, we report a (3 + 2) cycloaddition\nof pyrazolone MBH carbonates with arynes, enabling the efficient synthesis\nof diverse indene-fused spiropyrazolones. The key is employing a new\nbifunctional Lewis base catalyst to facilitate the cycloaddition of <i>in situ</i> generated allylic pyridinium ylides with arynes.

Figshare
Openalex Percentile: Top 76%
Cyclization and Aryne Chemistry
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Bifunctional\nLewis Base-Catalyzed (3 + 2) Cycloadditions\nof Pyrazolone-Derived MBH Carbonates with Arynes · Figshare (2024) | TGRS Research Map | TGRS