Potassium (E)-alkenylaryltrifluoroborates: Orthogonal functionalization of haloaryltrifluoroborates via heck-mizoroki reaction

Jung Ho Song; Taejung Kim; Jae Wook Lee; Soo Yeon Moon; Won Suk Kim; Jungyeob Ham

doi:10.1002/adsc.201300294

Potassium (E)-alkenylaryltrifluoroborates: Orthogonal functionalization of haloaryltrifluoroborates via heck-mizoroki reaction

Jung Ho Song, Taejung Kim, Jae Wook Lee, Soo Yeon Moon, Won Suk Kim, Jungyeob Ham

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

Abstract

A series of di- or trisubstituted alkenecontaining potassium organotrifluoroborates was prepared from the corresponding haloaryltrifluoroborates via palladium-catalyzed Heck-Mizoroki reaction with various olefins in good to excellent yields. Furthermore, the Suzuki-Miyaura cross-coupling reaction of these alkenylaryltrifluoroborates was successfully carried out with aryl and alkenyl bromides using 5 mol% of tetrakis(triphenylphosphine) palladium(0) and 3.0 equiv. of cesium carbonate in aqueous 1,4-dioxane under microwave irradiation.

Original language	English
Pages (from-to)	2459-2465
Number of pages	7
Journal	Advanced Synthesis and Catalysis
Volume	355
Issue number	11-12
DOIs	https://doi.org/10.1002/adsc.201300294
State	Published - 12 Aug 2013

Keywords

Heck-Mizoroki reaction
Microwave irradiation
Potassium (E)- alkenylaryltrifluoroborates
Suzuki-Miyaura reaction

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10.1002/adsc.201300294

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title = "Potassium (E)-alkenylaryltrifluoroborates: Orthogonal functionalization of haloaryltrifluoroborates via heck-mizoroki reaction",

abstract = "A series of di- or trisubstituted alkenecontaining potassium organotrifluoroborates was prepared from the corresponding haloaryltrifluoroborates via palladium-catalyzed Heck-Mizoroki reaction with various olefins in good to excellent yields. Furthermore, the Suzuki-Miyaura cross-coupling reaction of these alkenylaryltrifluoroborates was successfully carried out with aryl and alkenyl bromides using 5 mol% of tetrakis(triphenylphosphine) palladium(0) and 3.0 equiv. of cesium carbonate in aqueous 1,4-dioxane under microwave irradiation.",

keywords = "Heck-Mizoroki reaction, Microwave irradiation, Potassium (E)- alkenylaryltrifluoroborates, Suzuki-Miyaura reaction",

author = "Song, {Jung Ho} and Taejung Kim and Lee, {Jae Wook} and Moon, {Soo Yeon} and Kim, {Won Suk} and Jungyeob Ham",

year = "2013",

month = aug,

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doi = "10.1002/adsc.201300294",

language = "English",

volume = "355",

pages = "2459--2465",

journal = "Advanced Synthesis and Catalysis",

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TY - JOUR

T1 - Potassium (E)-alkenylaryltrifluoroborates

T2 - Orthogonal functionalization of haloaryltrifluoroborates via heck-mizoroki reaction

AU - Song, Jung Ho

AU - Kim, Taejung

AU - Lee, Jae Wook

AU - Moon, Soo Yeon

AU - Kim, Won Suk

AU - Ham, Jungyeob

PY - 2013/8/12

Y1 - 2013/8/12

N2 - A series of di- or trisubstituted alkenecontaining potassium organotrifluoroborates was prepared from the corresponding haloaryltrifluoroborates via palladium-catalyzed Heck-Mizoroki reaction with various olefins in good to excellent yields. Furthermore, the Suzuki-Miyaura cross-coupling reaction of these alkenylaryltrifluoroborates was successfully carried out with aryl and alkenyl bromides using 5 mol% of tetrakis(triphenylphosphine) palladium(0) and 3.0 equiv. of cesium carbonate in aqueous 1,4-dioxane under microwave irradiation.

AB - A series of di- or trisubstituted alkenecontaining potassium organotrifluoroborates was prepared from the corresponding haloaryltrifluoroborates via palladium-catalyzed Heck-Mizoroki reaction with various olefins in good to excellent yields. Furthermore, the Suzuki-Miyaura cross-coupling reaction of these alkenylaryltrifluoroborates was successfully carried out with aryl and alkenyl bromides using 5 mol% of tetrakis(triphenylphosphine) palladium(0) and 3.0 equiv. of cesium carbonate in aqueous 1,4-dioxane under microwave irradiation.

KW - Heck-Mizoroki reaction

KW - Microwave irradiation

KW - Potassium (E)- alkenylaryltrifluoroborates

KW - Suzuki-Miyaura reaction

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U2 - 10.1002/adsc.201300294

DO - 10.1002/adsc.201300294

M3 - Article

AN - SCOPUS:84884503291

SN - 1615-4150

VL - 355

SP - 2459

EP - 2465

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 11-12

ER -

Potassium (E)-alkenylaryltrifluoroborates: Orthogonal functionalization of haloaryltrifluoroborates via heck-mizoroki reaction

Abstract

Keywords

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