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空间位阻较大、具有受限催化灵活性的双恶唑啉衍生的N-杂环卡宾配体。

Sterically demanding, bioxazoline-derived N-heterocyclic carbene ligands with restricted flexibility for catalysis.

作者信息

Altenhoff Gereon, Goddard Richard, Lehmann Christian W, Glorius Frank

机构信息

Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany.

出版信息

J Am Chem Soc. 2004 Nov 24;126(46):15195-201. doi: 10.1021/ja045349r.

DOI:10.1021/ja045349r
PMID:15548016
Abstract

A unique family of N-heterocyclic carbenes derived from bioxazolines (IBiox) suitable for application in transition-metal catalysis is described. The ligands are electron rich, sterically demanding, and have restricted flexibility. Their usefulness has been demonstrated in the Suzuki-Miyaura cross-coupling of sterically hindered aryl chlorides and boronic acids. For the first time, tetraortho-substituted biaryls with methyl and larger ortho-substituents have been synthesized from aryl chlorides using the Suzuki-Miyaura method.

摘要

本文描述了一类独特的源自生物恶唑啉(IBiox)的N-杂环卡宾,适用于过渡金属催化。这些配体电子丰富、空间位阻大且具有受限的灵活性。它们在空间位阻较大的芳基氯与硼酸的铃木-宫浦交叉偶联反应中的实用性已得到证明。首次使用铃木-宫浦方法从芳基氯合成了具有甲基和更大邻位取代基的四邻位取代联芳基。

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Sterically demanding, bioxazoline-derived N-heterocyclic carbene ligands with restricted flexibility for catalysis.空间位阻较大、具有受限催化灵活性的双恶唑啉衍生的N-杂环卡宾配体。
J Am Chem Soc. 2004 Nov 24;126(46):15195-201. doi: 10.1021/ja045349r.
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Surveying sterically demanding N-heterocyclic carbene ligands with restricted flexibility for palladium-catalyzed cross-coupling reactions.研究具有受限灵活性的空间位阻较大的N-杂环卡宾配体在钯催化交叉偶联反应中的应用。
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A general method for the Suzuki-Miyaura cross-coupling of sterically hindered aryl chlorides: synthesis of di- and tri-ortho-substituted biaryls in 2-propanol at room temperature.一种用于空间位阻芳基氯的铃木-宫浦交叉偶联的通用方法:在室温下于2-丙醇中合成二邻位和三邻位取代的联芳基化合物。
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Simple (imidazol-2-ylidene)-Pd-acetate complexes as effective precatalysts for sterically hindered Suzuki-Miyaura couplings.简单的(咪唑-2-亚基)-钯-乙酸盐配合物作为空间位阻Suzuki-Miyaura偶联反应的有效预催化剂。
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Suzuki-Miyaura, alpha-ketone arylation and dehalogenation reactions catalyzed by a versatile N-heterocyclic carbene-palladacycle complex.铃木-宫浦反应、α-酮芳基化反应以及由一种多功能氮杂环卡宾-钯环配合物催化的脱卤反应。
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Highly active palladium catalysts supported by bulky proazaphosphatrane ligands for Stille cross-coupling: coupling of aryl and vinyl chlorides, room temperature coupling of aryl bromides, coupling of aryl triflates, and synthesis of sterically hindered biaryls.用于Stille交叉偶联的由大位阻前氮磷杂环卡宾配体负载的高活性钯催化剂:芳基和乙烯基氯的偶联、芳基溴的室温偶联、芳基三氟甲磺酸酯的偶联以及位阻联芳基的合成。
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