Reactivity of aryldimesitylboranes under suzuki-miyaura coupling conditions

Nan Wang; Zachary M. Hudson; Suning Wang

doi:10.1021/om1006903

Reactivity of aryldimesitylboranes under suzuki-miyaura coupling conditions

Nan Wang
, Zachary M. Hudson
, Suning Wang^*

^*Corresponding author for this work

Queen's University Kingston

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

13 Citations (Scopus)

Abstract

Sterically protected triarylboron compounds such as BMes₂(Ar) have important applications in organic optoelectronic devices and chemical sensors. Furthermore, the Suzuki-Miyaura cross-coupling reaction is the most commonly used method for building the π skeletons of such conjugated materials. We have found that BMes₂(Ar) can also be a highly active and effective coupling partner under typical Suzuki-Miyaura coupling conditions. For BMes₂(p-Br-Ph), self-coupling leads to the formation of oligomers Mes₂B-(Ph)_n-Mes, where the products with n = 1 (1), 2 (2), 3 (3), 4 (4) have been isolated and fully characterized. Examination of cross-coupling reactions of BMes₂(Ph) with various aryl bromides has established the generality of BMes₂(Ar) as a coupling partner.

Original language	English
Pages (from-to)	4007-4011
Number of pages	5
Journal	Organometallics
Volume	29
Issue number	18
DOIs	https://doi.org/10.1021/om1006903
Publication status	Published - 27 Sept 2010
Externally published	Yes

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title = "Reactivity of aryldimesitylboranes under suzuki-miyaura coupling conditions",

abstract = "Sterically protected triarylboron compounds such as BMes2(Ar) have important applications in organic optoelectronic devices and chemical sensors. Furthermore, the Suzuki-Miyaura cross-coupling reaction is the most commonly used method for building the π skeletons of such conjugated materials. We have found that BMes2(Ar) can also be a highly active and effective coupling partner under typical Suzuki-Miyaura coupling conditions. For BMes2(p-Br-Ph), self-coupling leads to the formation of oligomers Mes2B-(Ph)n-Mes, where the products with n = 1 (1), 2 (2), 3 (3), 4 (4) have been isolated and fully characterized. Examination of cross-coupling reactions of BMes2(Ph) with various aryl bromides has established the generality of BMes2(Ar) as a coupling partner.",

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T1 - Reactivity of aryldimesitylboranes under suzuki-miyaura coupling conditions

AU - Wang, Nan

AU - Hudson, Zachary M.

AU - Wang, Suning

PY - 2010/9/27

Y1 - 2010/9/27

N2 - Sterically protected triarylboron compounds such as BMes2(Ar) have important applications in organic optoelectronic devices and chemical sensors. Furthermore, the Suzuki-Miyaura cross-coupling reaction is the most commonly used method for building the π skeletons of such conjugated materials. We have found that BMes2(Ar) can also be a highly active and effective coupling partner under typical Suzuki-Miyaura coupling conditions. For BMes2(p-Br-Ph), self-coupling leads to the formation of oligomers Mes2B-(Ph)n-Mes, where the products with n = 1 (1), 2 (2), 3 (3), 4 (4) have been isolated and fully characterized. Examination of cross-coupling reactions of BMes2(Ph) with various aryl bromides has established the generality of BMes2(Ar) as a coupling partner.

AB - Sterically protected triarylboron compounds such as BMes2(Ar) have important applications in organic optoelectronic devices and chemical sensors. Furthermore, the Suzuki-Miyaura cross-coupling reaction is the most commonly used method for building the π skeletons of such conjugated materials. We have found that BMes2(Ar) can also be a highly active and effective coupling partner under typical Suzuki-Miyaura coupling conditions. For BMes2(p-Br-Ph), self-coupling leads to the formation of oligomers Mes2B-(Ph)n-Mes, where the products with n = 1 (1), 2 (2), 3 (3), 4 (4) have been isolated and fully characterized. Examination of cross-coupling reactions of BMes2(Ph) with various aryl bromides has established the generality of BMes2(Ar) as a coupling partner.

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U2 - 10.1021/om1006903

DO - 10.1021/om1006903

M3 - Article

AN - SCOPUS:77956927127

SN - 0276-7333

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SP - 4007

EP - 4011

JO - Organometallics

JF - Organometallics

IS - 18

ER -

Reactivity of aryldimesitylboranes under suzuki-miyaura coupling conditions

Abstract

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