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通过二芳基甲烷的串联芳基化/氧化反应合成三芳基甲醇。

Synthesis of triarylmethanols via tandem arylation/oxidation of diarylmethanes.

作者信息

Mao Jianyou, Eberle Kelly, Zhang Jiadi, Rodriguez Carles, Xi Zhenfeng, Pericàs Miquel A, Walsh Patrick J

机构信息

Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing 100193, P. R. China ; Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.

Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.

出版信息

Tetrahedron Lett. 2015 Jun 3;56(23):3604-3607. doi: 10.1016/j.tetlet.2015.01.189.

DOI:10.1016/j.tetlet.2015.01.189
PMID:26034337
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4448728/
Abstract

A tandem arylation/oxidation of diarylmethanes for the convenient synthesis of unsymmetrical triarylmethanols bearing different aryl and heteroaryl groups is described. A Pd(OAc)-NiXantphos catalyst system efficiently catalyzed arylation of weakly acidic sp-hybridized C-H bonds of diarylmethanes with aryl bromides, and the arylation products were then oxidized in situ to carbinols by simply opening the reaction flasks to air. The triarylmethanol products were obtained in 35-98% yield.

摘要

本文描述了一种通过二芳基甲烷的串联芳基化/氧化反应,便捷合成带有不同芳基和杂芳基的不对称三芳基甲醇的方法。Pd(OAc)-NiXantphos催化剂体系能有效催化二芳基甲烷中弱酸性sp杂化C-H键与芳基溴的芳基化反应,然后通过简单地打开反应瓶让空气进入,使芳基化产物原位氧化为甲醇。三芳基甲醇产物的产率为35 - 98%。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b35b/4448728/f448c562904d/nihms-661873-f0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b35b/4448728/8ea2a8689f2c/nihms-661873-f0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b35b/4448728/4152152d498f/nihms-661873-f0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b35b/4448728/f448c562904d/nihms-661873-f0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b35b/4448728/8ea2a8689f2c/nihms-661873-f0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b35b/4448728/4152152d498f/nihms-661873-f0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b35b/4448728/f448c562904d/nihms-661873-f0003.jpg

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本文引用的文献

1
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Org Biomol Chem. 2014 Nov 14;12(42):8488-98. doi: 10.1039/c4ob01594k.
2
Palladium-catalyzed α-arylation of benzylic phosphine oxides.钯催化的苄基膦氧化物的α-芳基化反应。
Org Lett. 2014 Jan 3;16(1):130-3. doi: 10.1021/ol403124g. Epub 2013 Dec 2.
3
Raising the pKa limit of "soft" nucleophiles in palladium-catalyzed allylic substitutions: application of diarylmethane pronucleophiles.
双金属催化剂作用下甲苯的苄基芳基化反应中的阳离子-π 相互作用。
J Am Chem Soc. 2018 Oct 3;140(39):12415-12423. doi: 10.1021/jacs.8b05143. Epub 2018 Sep 19.
4
Tandem C(sp)-H Arylation/Oxidation and Arylation/Allylic Substitution of Isoindolinones.异吲哚啉酮的串联C(sp)-H芳基化/氧化及芳基化/烯丙基取代反应
Adv Synth Catal. 2016 Sep 1;358(17):2829-2837. doi: 10.1002/adsc.201600654. Epub 2016 Aug 2.
5
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Chem Sci. 2016 Feb;7(2):976-983. doi: 10.1039/C5SC02739J. Epub 2015 Oct 27.
6
Palladium-Catalyzed Benzylic Arylation of Pyridylmethyl Silyl Ethers: One-Pot Synthesis of Aryl(pyridyl)methanols.钯催化吡啶基甲基硅醚的苄基芳基化反应:芳基(吡啶基)甲醇的一锅法合成
Org Lett. 2016 Apr 1;18(7):1590-3. doi: 10.1021/acs.orglett.6b00450. Epub 2016 Mar 23.
7
Palladium-Catalyzed Benzylic C-H Arylation of Azaarylmethylamines.钯催化氮杂芳基甲胺的苄基C-H芳基化反应
Org Lett. 2015 Dec 4;17(23):5788-5791. doi: 10.1021/acs.orglett.5b02898. Epub 2015 Nov 17.
提高钯催化烯丙基取代反应中“软”亲核试剂的 pKa 限制:二芳基甲烷给电子体的应用。
J Am Chem Soc. 2013 Nov 20;135(46):17602-9. doi: 10.1021/ja409511n. Epub 2013 Nov 12.
4
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Org Biomol Chem. 2013 Oct 7;11(37):6246-9. doi: 10.1039/c3ob41488d.
5
Palladium-catalyzed direct intermolecular α-arylation of amides with aryl chlorides.钯催化的酰胺与芳基氯的直接分子间 α-芳基化反应。
Org Lett. 2013 Aug 16;15(16):4190-3. doi: 10.1021/ol4019002. Epub 2013 Aug 5.
6
Palladium-catalyzed direct α-arylation of methyl sulfones with aryl bromides.钯催化的甲基砜与芳基溴化物的直接 α-芳基化反应。
Org Lett. 2013 Apr 5;15(7):1690-3. doi: 10.1021/ol400472v. Epub 2013 Mar 21.
7
Palladium-catalyzed direct arylation of methyl sulfoxides with aryl halides.钯催化的甲基亚砜与芳基卤化物的直接芳基化反应。
J Am Chem Soc. 2013 Mar 13;135(10):3740-3. doi: 10.1021/ja4009776. Epub 2013 Feb 27.
8
Asymmetric cross-coupling of aryl triflates to the benzylic position of benzylamines.芳基三氟甲磺酸酯与苄胺苄基位置的不对称交叉偶联反应。
Angew Chem Int Ed Engl. 2012 Nov 12;51(46):11510-3. doi: 10.1002/anie.201201874. Epub 2012 Oct 4.
9
Palladium-catalyzed C(sp3)-H arylation of diarylmethanes at room temperature: synthesis of triarylmethanes via deprotonative-cross-coupling processes.钯催化的室温下二芳基甲烷的 C(sp3)-H 芳基化反应:通过去质子交叉偶联过程合成三芳基甲烷。
J Am Chem Soc. 2012 Aug 22;134(33):13765-72. doi: 10.1021/ja3047816. Epub 2012 Aug 7.
10
Albopunctatone, an antiplasmodial anthrone-anthraquinone from the Australian ascidian Didemnum albopunctatum.从澳大利亚的 Didemnum albopunctatum 中分离得到的抗疟原虫蒽酮-蒽醌化合物 Albopunctatone。
J Nat Prod. 2012 Jun 22;75(6):1206-9. doi: 10.1021/np300074z. Epub 2012 Jun 8.