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通过蒽醌衍生物的选择性C-H/C-O芳基化高效合成3,6,13,16-四取代-四苯并[,,,]蔻

Efficient synthesis of 3,6,13,16-tetrasubstituted-tetrabenzo[,,,]coronenes by selective C-H/C-O arylations of anthraquinone derivatives.

作者信息

Terai Seiya, Sato Yuki, Kochi Takuya, Kakiuchi Fumitoshi

机构信息

Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.

出版信息

Beilstein J Org Chem. 2020 Mar 31;16:544-550. doi: 10.3762/bjoc.16.51. eCollection 2020.

DOI:10.3762/bjoc.16.51
PMID:32280384
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7136549/
Abstract

An efficient synthesis of tetrabenzo[,,,]coronene derivatives having alkyl and alkoxy substituents at the 3, 6, 13, and 16-positions was achieved based on the ruthenium-catalyzed coupling reactions of anthraquinone derivatives with arylboronates via C-H and C-O bond cleavage. The reaction sequence involving the arylation, carbonyl methylenation, and oxidative cyclization effectively provided various tetrabenzo[,,,]coronenes in short steps from readily available starting materials. Tetrabenzo[,,,]coronenes possessing two different types of substituents were obtained selectively by sequential chemoselective C-O arylation and C-H arylation. The H NMR spectra of the tetrabenzo[,,,]coronene product indicated its self-assembling behavior in CDCl.

摘要

基于蒽醌衍生物与芳基硼酸酯通过C-H和C-O键裂解的钌催化偶联反应，实现了在3、6、13和16位具有烷基和烷氧基取代基的四苯并[,,,]蒄衍生物的高效合成。涉及芳基化、羰基亚甲基化和氧化环化的反应序列从易得的起始原料出发，通过短步骤有效地提供了各种四苯并[,,,]蒄。通过顺序化学选择性C-O芳基化和C-H芳基化选择性地获得了具有两种不同类型取代基的四苯并[,,,]蒄。四苯并[,,,]蒄产物的1H NMR光谱表明其在CDCl3中的自组装行为。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e6e7/7136549/eab9b510c4f0/Beilstein_J_Org_Chem-16-544-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e6e7/7136549/0db404a05647/Beilstein_J_Org_Chem-16-544-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e6e7/7136549/bc3c91053131/Beilstein_J_Org_Chem-16-544-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e6e7/7136549/20ae36d29b73/Beilstein_J_Org_Chem-16-544-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e6e7/7136549/5336c391b098/Beilstein_J_Org_Chem-16-544-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e6e7/7136549/d48d4b870a20/Beilstein_J_Org_Chem-16-544-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e6e7/7136549/eab9b510c4f0/Beilstein_J_Org_Chem-16-544-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e6e7/7136549/0db404a05647/Beilstein_J_Org_Chem-16-544-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e6e7/7136549/bc3c91053131/Beilstein_J_Org_Chem-16-544-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e6e7/7136549/20ae36d29b73/Beilstein_J_Org_Chem-16-544-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e6e7/7136549/5336c391b098/Beilstein_J_Org_Chem-16-544-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e6e7/7136549/d48d4b870a20/Beilstein_J_Org_Chem-16-544-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e6e7/7136549/eab9b510c4f0/Beilstein_J_Org_Chem-16-544-g003.jpg

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Selective Monoarylation of Aromatic Ketones via C-H Bond Cleavage by Trialkylphosphine Ruthenium Catalysts.通过三烷基膦钌催化剂的碳氢键裂解实现芳族酮的选择性单芳基化反应。
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Selective Monoarylation of Aromatic Ketones and Esters via Cleavage of Aromatic Carbon-Heteroatom Bonds by Trialkylphosphine Ruthenium Catalysts.三烷基膦钌催化剂促进的芳基酮和酯的选择性单芳基化反应：芳杂原子键的断裂
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