实用的一锅法碳氢键活化/硼化/氧化反应：多克规模制备3-溴-5-甲基苯酚
Practical One-Pot C-H Activation/Borylation/Oxidation: Preparation of 3-Bromo-5-methylphenol on a Multigram Scale.
作者信息
Norberg A Monica, Smith Milton R, Maleczka Robert E
机构信息
Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA.
出版信息
Synthesis (Stuttg). 2011 Mar;2011(6):857-859. doi: 10.1055/s-0030-1258443. Epub 2011 Feb 18.
Abstract
A practical one-pot C-H activation/borylation/oxidation sequence for the generation of 3,5-disubstituted phenols is presented. Specifically, 3-bromo-5-methylphenol is prepared from 3-bromotoluene, without isolation of intermediates, on a multigram scale, and in high yield. The process proceeds under mild conditions and can be completed within one day.
摘要
本文介绍了一种实用的一锅法C-H活化/硼化/氧化序列，用于生成3,5-二取代苯酚。具体而言，以3-溴甲苯为原料，无需分离中间体，即可大规模、高产率地制备3-溴-5-甲基苯酚。该过程在温和条件下进行，一天内即可完成。
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本文引用的文献
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Chem Commun (Camb). 2010 Nov 7;46(41):7724-6. doi: 10.1039/c0cc02041a. Epub 2010 Sep 20.
2
C-H activation for the construction of C-B bonds.用于构建碳-硼键的碳-氢活化反应。
Chem Rev. 2010 Feb 10;110(2):890-931. doi: 10.1021/cr900206p.
3
Mechanism of the mild functionalization of arenes by diboron reagents catalyzed by iridium complexes. Intermediacy and chemistry of bipyridine-ligated iridium trisboryl complexes.铱配合物催化二硼试剂对芳烃的温和官能团化反应机理。联吡啶配位的三硼化铱配合物的中间体及化学性质。
J Am Chem Soc. 2005 Oct 19;127(41):14263-78. doi: 10.1021/ja053433g.
4
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5
Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds.用于构建芳香族碳氢键的极具选择性的铱催化剂。
Science. 2002 Jan 11;295(5553):305-8. doi: 10.1126/science.1067074. Epub 2001 Nov 22.
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