Fluoride-Catalyzed Cross-Coupling of Carbamoyl Fluorides and Alkynylsilanes

被引：12

作者：

Cadwallader, Dusty ^{[1
]}

Shevchuk, Dmytro ^{[1
]}

Tiburcio, Tristan R. ^{[1
]}

Le, Christine M. ^{[1
]}

机构：

[1] York Univ, Dept Chem, Toronto, ON M3J 1P3, Canada

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 40期

基金：

加拿大自然科学与工程研究理事会;

关键词：

OXIDATIVE AMINOCARBONYLATION; CONVENIENT SYNTHESIS; N-ARYLPROPIOLAMIDES; ROUTE; IODOCYCLIZATION; SILYLACETYLENES; CYCLIZATION; EFFICIENT; KETONES;

D O I：

10.1021/acs.orglett.3c02871

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report the synthesis of alkynamides via the cross-coupling of carbamoyl fluorides and alkynylsilanes catalyzed by tetrabutylammonium fluoride (TBAF). In contrast to previously reported transformations of carbamoyl fluorides, C-F bond cleavage is achieved under exceptionally mild conditions (room temperature, low catalyst loadings, and short reaction times) without the need for strongly nucleophilic reagents and/or catalysts. This method offers distinct advantages over transition-metal-catalyzed approaches, such as tolerance to aryl halide moieties and complementary chemoselectivity.

引用

收藏

页码：7369 / 7373

页数：5

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