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光催化顺序C-H官能化加速咪唑杂环的乙酰氧基丙二酸酯化反应

Photocatalytic sequential C-H functionalization expediting acetoxymalonylation of imidazo heterocycles.

作者信息

Singh Deepak, Pramanik Shyamal, Maity Soumitra

机构信息

Department of Chemistry and Chemical Biology, Indian Institute of Technology (ISM) Dhanbad, JH 826004, India.

出版信息

Beilstein J Org Chem. 2023 May 12;19:666-673. doi: 10.3762/bjoc.19.48. eCollection 2023.

DOI:10.3762/bjoc.19.48
PMID:37205129
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10186259/
Abstract

The importance of functionalized imidazo heterocycles has often been featured in several impactful research both from academia and industry. Herein, we report a direct C-3 acetoxymalonylation of imidazo heterocycles using relay C-H functionalization enabled by organophotocatalysis starring zinc acetate in the triple role of an activator, ion scavenger as well as an acetylating reagent. The mechanistic investigation revealed a sequential sp and sp C-H activation, followed by functionalization driven by zinc acetate coupled with the photocatalyst PTH. A variety of imidazo[1,2-]pyridines and related heterocycles were explored as substrates along with several active methylene reagents, all generating the products with excellent yields and regioselectivity, thus confirming excellent functional group tolerability.

摘要

功能化咪唑杂环的重要性在学术界和工业界的多项有影响力的研究中经常得到体现。在此，我们报道了利用有机光催化实现的接力C-H官能化反应，对咪唑杂环进行直接的C-3乙酰氧基丙二酸酯化反应，其中醋酸锌发挥了活化剂、离子清除剂以及乙酰化试剂的三重作用。机理研究表明，反应过程中先进行sp和sp C-H活化，随后由醋酸锌与光催化剂PTH共同驱动官能化反应。我们考察了多种咪唑并[1,2-]吡啶及相关杂环作为底物，以及几种活性亚甲基试剂，所有反应均以优异的产率和区域选择性生成产物，从而证实了该反应对官能团具有出色的耐受性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fad1/10186259/51cfebad1b1d/Beilstein_J_Org_Chem-19-666-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fad1/10186259/27e465425c82/Beilstein_J_Org_Chem-19-666-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fad1/10186259/f8b35f503b42/Beilstein_J_Org_Chem-19-666-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fad1/10186259/356bcdc97594/Beilstein_J_Org_Chem-19-666-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fad1/10186259/51cfebad1b1d/Beilstein_J_Org_Chem-19-666-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fad1/10186259/27e465425c82/Beilstein_J_Org_Chem-19-666-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fad1/10186259/f8b35f503b42/Beilstein_J_Org_Chem-19-666-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fad1/10186259/356bcdc97594/Beilstein_J_Org_Chem-19-666-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fad1/10186259/51cfebad1b1d/Beilstein_J_Org_Chem-19-666-g005.jpg

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