无金属条件下有机三氟硼酸盐的脱硼氯代反应。
Metal-free chlorodeboronation of organotrifluoroborates.
机构信息
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
出版信息
J Org Chem. 2011 Sep 2;76(17):7195-203. doi: 10.1021/jo201313a. Epub 2011 Aug 3.
Abstract
A mild and metal-free method for the chlorodeboronation of organotrifluoroborates using trichloroisocyanuric acid (TCICA) was developed. Aryl-, heteroaryl-, alkenyl-, alkynyl-, and alkyltrifluoroborates were converted into the corresponding chlorinated products in good yields. This method proved to be tolerant of a broad range of functional groups.
摘要
开发了一种温和、无金属的方法，使用三氯异氰尿酸（TCICA）对有机三氟硼酸盐进行氯代脱硼反应。芳基、杂芳基、烯基、炔基和烷基三氟硼酸盐以良好的收率转化为相应的氯化产物。该方法被证明对广泛的官能团具有耐受性。
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1
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Org Lett. 2011 Apr 1;13(7):1852-5. doi: 10.1021/ol2003572. Epub 2011 Mar 10.
2
Nickel-catalyzed cross-coupling of potassium aryl- and heteroaryltrifluoroborates with unactivated alkyl halides.镍催化的钾芳基和杂芳基三氟硼酸盐与未活化的烷基卤化物的交叉偶联反应。
Org Lett. 2010 Dec 17;12(24):5783-5. doi: 10.1021/ol102717x. Epub 2010 Nov 19.
3
Gold(III)-catalyzed halogenation of aromatic boronates with N-halosuccinimides.金(III)催化的 N-卤代琥珀酰亚胺与芳基硼酸酯的卤化反应。
Org Lett. 2010 Dec 3;12(23):5474-7. doi: 10.1021/ol102350v. Epub 2010 Nov 11.
4
Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of enantiomerically enriched potassium β-trifluoroboratoamides with various aryl- and hetaryl chlorides.钯催化的对映体富集的钾 β-三氟硼酸盐酰胺与各种芳基和杂芳基氯化物的 Suzuki-Miyaura 交叉偶联反应。
Org Lett. 2010 Oct 1;12(19):4384-7. doi: 10.1021/ol101865e.
5
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Chemistry. 2010 Jul 19;16(27):8155-61. doi: 10.1002/chem.201000401.
6
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8
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9
Gold-catalyzed halogenation of aromatics by N-halosuccinimides.N-卤代琥珀酰亚胺对芳烃的金催化卤化反应。
Angew Chem Int Ed Engl. 2010 Mar 8;49(11):2028-32. doi: 10.1002/anie.200906699.
10
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