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金催化下稳定的乙烯基重氮化合物对烯基硅烷和炔基硅烷的反应活性：跳烯和烯炔的区域和立体选择性合成

Reactivity of Stabilized Vinyldiazo Compounds toward Alkenyl- and Alkynylsilanes under Gold Catalysis: Regio- and Stereoselective Synthesis of Skipped Dienes and Enynes.

作者信息

Bernardo Olaya, Yamamoto Kota, Fernández Israel, López Luis A

机构信息

Departamento de Química Orgánica e Inorgánica, Instituto Universitario de Química Organometálica "Enrique Moles and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Oviedo, Julián Clavería 8, 33006-Oviedo, Spain.

Departamento de Química Orgánica I and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Facultad de Ciencias Químicas, Universidad Complutense de Madrid, 28040-Madrid, Spain.

出版信息

Org Lett. 2021 Jun 4;23(11):4452-4456. doi: 10.1021/acs.orglett.1c01381. Epub 2021 May 13.

DOI:10.1021/acs.orglett.1c01381
PMID:33983038
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8900156/
Abstract

We report the gold-catalyzed reaction of vinyldiazo compounds and alkenylsilanes to produce skipped dienes, which are common structural motifs in an array of bioactive compounds. This carbon-carbon bond-forming transformation proceeds with complete regio- and stereoselectivity with the silyl group serving as a regio- and stereocontrolling element. Likewise, the use of alkynylsilanes as reaction partners yielded skipped enynes resulting from a C(sp)-C(sp) coupling. Mechanistic experiments and DFT studies have provided support for a stepwise mechanism.

摘要

我们报道了乙烯基重氮化合物与烯基硅烷的金催化反应，该反应生成了跳跃式二烯，这是一系列生物活性化合物中常见的结构基序。这种碳-碳键形成转化以完全的区域和立体选择性进行，硅基作为区域和立体控制元素。同样，使用炔基硅烷作为反应伙伴可通过C(sp)-C(sp)偶联生成跳跃式烯炔。机理实验和密度泛函理论研究为逐步机理提供了支持。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a65/8900156/5e9f0d113cf5/ol1c01381_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a65/8900156/49a3dbf4c6fd/ol1c01381_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a65/8900156/906ec3733898/ol1c01381_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a65/8900156/d798ec2b44b7/ol1c01381_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a65/8900156/5e9f0d113cf5/ol1c01381_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a65/8900156/49a3dbf4c6fd/ol1c01381_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a65/8900156/906ec3733898/ol1c01381_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a65/8900156/d798ec2b44b7/ol1c01381_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a65/8900156/5e9f0d113cf5/ol1c01381_0007.jpg

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