2012
DOI: 10.1002/ejoc.201101783
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Suzuki–Miyaura Cross‐Coupling Reactions in a Solkane365/227/Ethanol Blend at Ambient Temperature

Abstract: An environmentally benign solvent system, Solkane365/227/ethanol blend, was developed for Suzuki–Miyaura cross‐coupling reactions of aryl boronic acids and aryl halides. The reaction is quite general and gives excellent yields for various aryl, heteroaryl, and fluoroaryl boronic acids or halides. Interestingly, this system also allows the synthesis of polyaryls.

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Cited by 20 publications
(6 citation statements)
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“…To functionalize the alkenyl aryl tetrafluorosulfanes, Suzuki coupling of the boronic acids 4 with 1 d formed 1 e – g , in good yields, and is consistent with coupling of pentafluorosulfany‐substituted arenes (Scheme ) 12. In contrast to the reaction of pentafluorosulfanyl aryl bromide, addition to 1 required a significantly higher reaction temperature of 120 °C, as opposed to room temperature.…”
Section: Methodssupporting
confidence: 57%
“…To functionalize the alkenyl aryl tetrafluorosulfanes, Suzuki coupling of the boronic acids 4 with 1 d formed 1 e – g , in good yields, and is consistent with coupling of pentafluorosulfany‐substituted arenes (Scheme ) 12. In contrast to the reaction of pentafluorosulfanyl aryl bromide, addition to 1 required a significantly higher reaction temperature of 120 °C, as opposed to room temperature.…”
Section: Methodssupporting
confidence: 57%
“…To functionalize the alkenyl aryl tetrafluorosulfanes, Suzuki coupling of the boronic acids 4 with 1 d formed 1 eg, in good yields, and is consistent with coupling of pentafluorosulfany-substituted arenes (Scheme 2). [12] In contrast to the reaction of pentafluorosulfanyl aryl bromide, addition to 1 required a significantly higher reaction temperature of 120 8C, as opposed to room temperature. A variety of solvent systems and temperatures were examined to determine the optimum reaction conditions for coupling reactions of 1.…”
mentioning
confidence: 99%
“…Recently, we reported the preparation of (3,5‐bis(pentafluoro‐ λ 6 ‐sulfanyl)phenyl)boronic acid ( 1 ) and its utility as an organocatalyst 5h. A boronic acid should also be attractive as a pentafluorosulfanyl‐aromatic building block under the Suzuki–Miyaura coupling reaction 8. As a part of our research program toward the design and synthesis of biologically active organofluorine compounds, we were interested in previously unknown (5‐azido‐1,3‐phenylene)bis(pentafluoro‐ λ 6 ‐sulfane) ( 2 ) as a new tool for click chemistry (Figure 1).…”
Section: Methodsmentioning
confidence: 99%