- Potassium trimethylsilanolate enables rapid, homogeneous suzuki-miyaura cross-coupling of boronic esters
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Herein, a mild and operationally simple method for the Suzuki-Miyaura cross-coupling of boronic esters is described. Central to this advance is the use of the organic-soluble base, potassium trimethylsilanolate, which allows for a homogeneous, anhydrous cross-coupling. The coupling proceeds at a rapid rate, often furnishing products in quantitative yield in less than 5 min. By applying this method, a >10-fold decrease in reaction time was observed for three published reactions which required >48 h to reach satisfactory conversion.
- Delaney, Connor P.,Kassel, Vincent M.,Denmark, Scott E.
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- Pd-Catalyzed Suzuki-Miyaura and Hiyama-Denmark Couplings of Aryl Sulfamates
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Using a recently discovered precatalyst, the first Pd-catalyzed Suzuki-Miyaura reactions using aryl sulfamates that occur at room temperature are reported. In complementary work, it is demonstrated that a related precatalyst can facilitate the coupling of aryl silanolates, which are less toxic and reactive nucleophiles than boronic acids with aryl chlorides. By combining our results using modern electrophiles and nucleophiles, the first Hiyama-Denmark reactions using aryl sulfamates are reported.
- Melvin, Patrick R.,Hazari, Nilay,Beromi, Megan Mohadjer,Shah, Hemali P.,Williams, Michael J.
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supporting information
p. 5784 - 5787
(2016/11/29)
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- 18-Crown-6 promoting Pd/C-catalyzed cross-coupling reaction of aryl bromides and arylboronic acids in aqueous media
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Pd/C-catalyzed Suzuki-Miyaura cross-coupling between aryl bromides and arylboronic acids in 50% methanol aqueous solution proceeded smoothly in the presence of 18-crown-6. Various aryl bromides bearing electron-withdrawing groups and electron-donating gro
- Chu, Wenyi,Li, Xinmin,Hou, Yanjun,Wang, Hua,Li, Hongyu,Yuan, Xiaobin,Sun, Zhizhong
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p. 478 - 482
(2012/10/29)
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- Synthesis and reactivity of solid-supported organotrifluoroborates in suzuki cross-coupling
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Solid-supported organotrifluoroborates were prepared in high yields by ion exchange with Amberlyst resins. The reactivity of solid supported aryltrifluoroborates was evaluated in Suzuki-Miyaura couplings with numerous aryl bromide partners. Electron-rich
- Colombel, Virginie,Presset, Marc,Oehlrich, Daniel,Rombouts, Frederik,Molander, Gary A.
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supporting information; experimental part
p. 1680 - 1683
(2012/06/30)
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- Palladium-indolylphosphine-catalyzed hiyama cross-coupling of aryl mesylates
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(Chemical Equation Presented) Aryl mesylates are found to be applicable as electrophiles in organosilicon-mediated coupling reactions. The catalyst system comprising 2 mol % of Pd(OAc)2 and CM-phos supporting ligand is highly effective in catalyzing Hiyama cross-coupling of various aryl and heteroaryl mesylates. Interesting acid additive effects show that the presence of 0.25-0.50 equiv of acetic acid efficiently suppresses the mesylate decomposition and generally promotes the coupling product yields.
- So, Chau Ming,Lee, Hang Wai,Lau, Chak Po,Kwong, Fuk Yee
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supporting information; experimental part
p. 317 - 320
(2009/07/04)
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