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获得碳（sp）硼化和硅化的环状分子：相应芳烃和杂芳烃的氢化反应。

Access to C(sp) borylated and silylated cyclic molecules: hydrogenation of corresponding arenes and heteroarenes.

作者信息

Chhabra Arzoo, Reich Sabrina, Shannon Timothy M, Maleczka Robert E, Smith Milton R

机构信息

Department of Chemistry, Michigan State University 578 S Shaw Lane East Lansing Michigan 48824 USA

出版信息

RSC Adv. 2024 Apr 2;14(15):10590-10607. doi: 10.1039/d4ra00491d. eCollection 2024 Mar 26.

DOI:10.1039/d4ra00491d
PMID:38567346
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10985595/
Abstract

This paper presents a simple and cost-effective hydrogenation method for synthesizing a myriad of cycloalkanes and saturated heterocycles bearing boryl or silyl substituents. The catalyst used are heterogeneous, readily available, bench stable, and recyclable. Also demonstrated is the application of the method to compounds that possess both boryl and silyl groups. When combined with Ir-catalyzed sp C-H borylation, such hydrogenations offer a two-step complementary alternative to direct sp C-H borylations that can suffer selectivity and reactivity issues. Of practical value to the community, complete stereochemical analyses of reported borylated compounds that were never fully characterized are reported herein.

摘要

本文介绍了一种简单且经济高效的氢化方法，用于合成多种带有硼基或硅基取代基的环烷烃和饱和杂环。所使用的催化剂为多相催化剂，易于获得，在实验室条件下稳定且可回收。该方法对同时含有硼基和硅基的化合物的应用也得到了证明。当与铱催化的sp C-H硼化反应相结合时，此类氢化反应为直接sp C-H硼化反应提供了一种两步互补替代方法，而直接sp C-H硼化反应可能存在选择性和反应性问题。本文报道了对从未得到充分表征的已报道硼化化合物进行的完整立体化学分析，这对该领域具有实际价值。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d614/10985595/26525ec2a657/d4ra00491d-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d614/10985595/c34f2016887f/d4ra00491d-f1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d614/10985595/121fa4b1cc4d/d4ra00491d-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d614/10985595/075968598ce5/d4ra00491d-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d614/10985595/26525ec2a657/d4ra00491d-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d614/10985595/c34f2016887f/d4ra00491d-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d614/10985595/258cb3a9ebc9/d4ra00491d-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d614/10985595/121fa4b1cc4d/d4ra00491d-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d614/10985595/075968598ce5/d4ra00491d-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d614/10985595/26525ec2a657/d4ra00491d-s4.jpg

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本文引用的文献

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Org Biomol Chem. 2024 Jan 31;22(5):1010-1017. doi: 10.1039/d3ob01860a.
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