Abstract
The nickel-catalyzed Suzuki–Miyaura coupling of aryl halides and phenol-derived substrates with aryl boronic acids using green solvents, such as 2-Me-THF and tert-amyl alcohol, is reported. This methodology employs the commercially available and air-stable precatalyst, NiCl2(PCy3)2, and gives biaryl products in synthetically useful to excellent yields. Using this protocol, bis(heterocyclic) frameworks can be assembled efficiently.
Citing Articles
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This article has been cited by 5 ACS Journal articles (5 most recent appear below).
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ArkaitzCorrea and RubenMartinJournal of the American Chemical Society2014 136 (20), 7253-7256A novel Ni-catalyzed reductive amidation of C(sp2)–O and C(sp3)–O electrophiles with isocyanates is described. This umpolung reaction allows for an unconventional preparation of benzamides using simple starting materials and easy-to-handle Ni catalysts.
Nickel Hydroxo Complexes as Intermediates in Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling
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Alec H.Christian, PeterMüller, and SebastienMonfetteOrganometallics2014 33 (9), 2134-2137The synthesis, characterization, and reactivity of intermediates formed in the Ni-catalyzed Suzuki–Miyaura cross-coupling (SMC) of an aryl chloride are described. Oxidative addition of 1-chloro-4-trifluoromethylbenzene (1) to a mixture of Ni(cod)2 and PCy...
Mechanisms and Origins of Switchable Chemoselectivity of Ni-Catalyzed C(aryl)–O and C(acyl)–O Activation of Aryl Esters with Phosphine Ligands
Xin Hong, Yong Liang, and K. N. HoukJournal of the American Chemical Society2014 136 (5), 2017-2025Mechanisms and Origins of Switchable Chemoselectivity of Ni-Catalyzed C(aryl)–O and C(acyl)–O Activation of Aryl Esters with Phosphine Ligands
XinHong, YongLiang, and K. N.HoukJournal of the American Chemical Society2014 136 (5), 2017-2025Many experiments have shown that nickel with monodentate phosphine ligands favors the C(aryl)–O activation over the C(acyl)–O activation for aryl esters. However, Itami and co-workers recently discovered that nickel with bidentate phosphine ligands can ...
Isolation, Structure, and Reactivity of an Arylnickel(II) Pivalate Complex in Catalytic C–H/C–O Biaryl Coupling
Kei Muto, Junichiro Yamaguchi, Aiwen Lei, and Kenichiro ItamiJournal of the American Chemical Society2013 135 (44), 16384-16387
これは 使える！！
返信削除Ni ＋ R2BH Conbination !!
有機ホウ素化合物の ラジカル反応性 を活用して タウの氾濫をコントロールできないだろうか？？ 多分 できるな！！
返信削除BH は還元性、B-OH は 弱酸性の プロトン酸。