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在回流的苯酚中，通过三苯基膦与芳基溴反应无金属合成芳基三苯基溴化鏻。

Metal-Free Synthesis of Aryltriphenylphosphonium Bromides by the Reaction of Triphenylphosphine with Aryl Bromides in Refluxing Phenol.

作者信息

Huang Wenhua, Zhong Chun-Hong

机构信息

Department of Chemistry, Tianjin University, 135 Yaguan Road, Tianjin 300354, P. R. China.

出版信息

ACS Omega. 2019 Apr 11;4(4):6690-6696. doi: 10.1021/acsomega.9b00568. eCollection 2019 Apr 30.

DOI:10.1021/acsomega.9b00568
PMID:31459795
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6648432/
Abstract

A metal-free synthesis of aryltriphenylphosphonium bromides by the reaction of triphenylphosphine with aryl bromides in refluxing phenol is developed. This reaction tolerates hydroxymethyl, hydroxyphenyl, and carboxyl groups in aryl bromides, allowing to synthesize multifunctional aryltriphenylphosphonium bromides, from which facile access to multifunctional aryldiphenylphosphines and their oxides by hydrolysis and subsequent reduction is exemplified. A two-step addition-elimination mechanism, with the elimination step being a fast step, is also proposed.

摘要

通过三苯基膦与芳基溴在回流苯酚中反应，开发了一种无金属合成芳基三苯基溴化鏻的方法。该反应能耐受芳基溴中的羟甲基、羟基苯基和羧基，从而能够合成多功能芳基三苯基溴化鏻，通过水解和随后的还原可以方便地从其中获得多功能芳基二苯基膦及其氧化物。还提出了一种两步加成-消除机理，其中消除步骤为快速步骤。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e671/6648432/e73c2ba73508/ao-2019-00568m_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e671/6648432/42a6f8305e7d/ao-2019-00568m_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e671/6648432/62b281dde950/ao-2019-00568m_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e671/6648432/e73c2ba73508/ao-2019-00568m_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e671/6648432/42a6f8305e7d/ao-2019-00568m_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e671/6648432/62b281dde950/ao-2019-00568m_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e671/6648432/e73c2ba73508/ao-2019-00568m_0003.jpg

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本文引用的文献

1
Phosphine Organocatalysis.膦有机催化。
Chem Rev. 2018 Oct 24;118(20):10049-10293. doi: 10.1021/acs.chemrev.8b00081. Epub 2018 Sep 27.
2
Nucleophilic arylation with tetraarylphosphonium salts.用四芳基鏻盐进行亲核芳基化反应。
Nat Commun. 2016 Jan 29;7:10337. doi: 10.1038/ncomms10337.
3
Hydrogen storage materials: room-temperature wet-chemistry approach toward mixed-metal borohydrides.储氢材料：室温湿化学法制备混合金属硼氢化物。
含硫代氨基脲和三苯基氧化膦部分的1,4-萘醌铜配合物；通过核磁共振、红外光谱、质谱、紫外光谱和密度泛函理论计算进行合成与鉴定
ACS Omega. 2022 Sep 16;7(38):34463-34475. doi: 10.1021/acsomega.2c04113. eCollection 2022 Sep 27.
4
Multiple Emission of Phosphonium Fluorophores Harnessed by the Pathways of Photoinduced Counterion Migration.通过光致抗衡离子迁移途径实现的鏻荧光团的多重发射
Angew Chem Int Ed Engl. 2022 May 2;61(19):e202115690. doi: 10.1002/anie.202115690. Epub 2022 Feb 24.
5
Synthesis of Aryldiphenylphosphine Oxides by Quaternization of Tertiary Diphenylphosphines with Aryl Bromides Followed by the Wittig Reaction.通过叔二苯基膦与芳基溴的季铵化反应，随后进行维蒂希反应合成芳基二苯基氧化膦。
ACS Omega. 2020 Jun 23;5(26):16010-16020. doi: 10.1021/acsomega.0c01413. eCollection 2020 Jul 7.
6
Cationic Organophosphorus Chromophores: A Diamond in the Rough among Ionic Dyes.阳离子有机磷发色团：离子染料中未经雕琢的璞玉。
Chemistry. 2021 Jan 7;27(2):537-552. doi: 10.1002/chem.202001853. Epub 2020 Oct 30.
7
Versatile Visible-Light-Driven Synthesis of Asymmetrical Phosphines and Phosphonium Salts.可见光驱动的不对称膦和鏻盐的通用合成
Chemistry. 2020 Dec 9;26(69):16374-16382. doi: 10.1002/chem.202002646. Epub 2020 Oct 30.
Angew Chem Int Ed Engl. 2015 Jan 19;54(4):1236-9. doi: 10.1002/anie.201408456. Epub 2014 Dec 2.
4
Ionic liquids of superior thermal stability.具有优越热稳定性的离子液体。
Chem Commun (Camb). 2013 Sep 7;49(69):7590-2. doi: 10.1039/c3cc44118k. Epub 2013 Jul 19.
5
Highly chemoselective metal-free reduction of phosphine oxides to phosphines.高化学选择性的无金属还原膦氧化物为膦。
J Am Chem Soc. 2012 Nov 7;134(44):18325-9. doi: 10.1021/ja3069165. Epub 2012 Oct 29.
6
Efficient synthesis of quaternary and P-stereogenic phosphonium triflates.高效合成季铵盐和 P-手性膦三氟甲磺酸酯。
Org Lett. 2010 Apr 2;12(7):1568-71. doi: 10.1021/ol100304c.
7
Rapid phosphorus(III) ligand evaluation utilising potassium selenocyanate.利用硒氰酸钾对磷（III）配体进行快速评估
Dalton Trans. 2008 Feb 7(5):650-7. doi: 10.1039/b712782k. Epub 2007 Nov 16.
8
Palladium-catalyzed synthesis of functionalized tetraarylphosphonium salts.钯催化合成功能化四芳基鏻盐。
J Org Chem. 2008 Jan 18;73(2):590-3. doi: 10.1021/jo702355c. Epub 2007 Dec 23.
9
Demand-based thiolate anion generation under virtually neutral conditions: influence of steric and electronic factors on chemo- and regioselective cleavage of aryl alkyl ethers.
J Org Chem. 2002 Sep 6;67(18):6406-14. doi: 10.1021/jo0256540.