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一种基于新型三价碘试剂的实用、温和且高效的酚类亲电溴化反应：PIDA-AlBr体系

Practical, mild and efficient electrophilic bromination of phenols by a new I(iii)-based reagent: the PIDA-AlBr system.

作者信息

Satkar Yuvraj, Ramadoss Velayudham, Nahide Pradip D, García-Medina Ernesto, Juárez-Ornelas Kevin A, Alonso-Castro Angel J, Chávez-Rivera Ruben, Jiménez-Halla J Oscar C, Solorio-Alvarado César R

机构信息

Universidad de Guanajuato, Departamento de Química, División de Ciencias Naturales y Exactas Campus Guanajuato, Cerro de la Venada S/N 36040 Guanajuato Gto. México

Universidad de Guanajuato, Departamento de Farmacia, División de Ciencias Naturales y Exactas Campus Guanajuato, Noria alta S/N 36050 Guanajuato Gto. México.

出版信息

RSC Adv. 2018 May 15;8(32):17806-17812. doi: 10.1039/c8ra02982b. eCollection 2018 May 14.

DOI:10.1039/c8ra02982b
PMID:35542081
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9080473/
Abstract

A practical electrophilic bromination procedure for phenols and phenol-ethers was developed under efficient and very mild reaction conditions. A broad scope of arenes was investigated, including the benzimidazole and carbazole core as well as analgesics such as naproxen and paracetamol. The new I(iii)-based brominating reagent PhIOAcBr is operationally easy to prepare by mixing PIDA and AlBr. Our DFT calculations suggest that this is likely the brominating active species, which is prepared or isolated after centrifugation. Its stability at 4 °C after preparation was confirmed over a period of one month and no significant loss of its reactivity was observed. Additionally, the gram-scale bromination of 2-naphthol proceeds with excellent yields. Even for sterically hindered substrates, a moderately good reactivity is observed.

摘要

在高效且温和的反应条件下，开发了一种用于酚类和酚醚的实用亲电溴化方法。研究了广泛的芳烃，包括苯并咪唑和咔唑核心以及萘普生和对乙酰氨基酚等镇痛药。新型基于I(iii)的溴化试剂PhIOAcBr通过混合PIDA和AlBr在操作上易于制备。我们的密度泛函理论计算表明，这可能是溴化活性物种，在离心后制备或分离得到。制备后在4°C下其稳定性在一个月内得到证实，未观察到其反应活性有明显损失。此外，2-萘酚的克级溴化反应产率优异。即使对于空间位阻较大的底物，也观察到了适度良好的反应活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7c4b/9080473/1e1361721dd9/c8ra02982b-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7c4b/9080473/dda7809c15cf/c8ra02982b-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7c4b/9080473/2b30e5eccb26/c8ra02982b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7c4b/9080473/932fb1b79fc7/c8ra02982b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7c4b/9080473/8cb29f0a8277/c8ra02982b-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7c4b/9080473/7dcfaa35e66a/c8ra02982b-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7c4b/9080473/1e1361721dd9/c8ra02982b-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7c4b/9080473/dda7809c15cf/c8ra02982b-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7c4b/9080473/2b30e5eccb26/c8ra02982b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7c4b/9080473/932fb1b79fc7/c8ra02982b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7c4b/9080473/8cb29f0a8277/c8ra02982b-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7c4b/9080473/7dcfaa35e66a/c8ra02982b-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7c4b/9080473/1e1361721dd9/c8ra02982b-s5.jpg

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