Highly chemoselective heterogeneous Pd-catalyzed biaryl synthesis from haloarenes: Reaction in an oil-in-water microemulsion

Sudip Mukhopadhyay; Anan Yaghmur; Mubeen Baidossi; Buddhadeb Kundu; Yoel Sasson

doi:10.1021/op020094s

Highly chemoselective heterogeneous Pd-catalyzed biaryl synthesis from haloarenes: Reaction in an oil-in-water microemulsion

Sudip Mukhopadhyay^*, Anan Yaghmur, Mubeen Baidossi, Buddhadeb Kundu, Yoel Sasson

^*Corresponding author for this work

22 Citations (Scopus)

Abstract

Heterogeneous Pd/C-catalyzed reductive coupling of substituted haloarenes to the respective biaryls is effected with very high chemoselectivity in an oil-in-water microemulsion, using a reducing agent such as formate and a base, NaOH, in the presence of a catalytic amount of tetrabutylammonium bromide (TBAB) at 75°C. Almost 100% biphenyl selectivity is obtained with iodobenzene. High coupling yields are achieved with 4-chlorotoluene and 4-chlorobenzaldehyde as the substrate. The competitive reduction reaction becomes predominant when the water-in-oil microemulsion is used as the solvent medium.

Original language	English
Journal	Organic Process Research and Development
Volume	7
Issue number	5
Pages (from-to)	641-643
Number of pages	3
ISSN	1083-6160
DOIs	https://doi.org/10.1021/op020094s
Publication status	Published - 1 Sept 2003

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abstract = "Heterogeneous Pd/C-catalyzed reductive coupling of substituted haloarenes to the respective biaryls is effected with very high chemoselectivity in an oil-in-water microemulsion, using a reducing agent such as formate and a base, NaOH, in the presence of a catalytic amount of tetrabutylammonium bromide (TBAB) at 75°C. Almost 100% biphenyl selectivity is obtained with iodobenzene. High coupling yields are achieved with 4-chlorotoluene and 4-chlorobenzaldehyde as the substrate. The competitive reduction reaction becomes predominant when the water-in-oil microemulsion is used as the solvent medium.",

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AU - Mukhopadhyay, Sudip

AU - Yaghmur, Anan

AU - Baidossi, Mubeen

AU - Kundu, Buddhadeb

AU - Sasson, Yoel

PY - 2003/9/1

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N2 - Heterogeneous Pd/C-catalyzed reductive coupling of substituted haloarenes to the respective biaryls is effected with very high chemoselectivity in an oil-in-water microemulsion, using a reducing agent such as formate and a base, NaOH, in the presence of a catalytic amount of tetrabutylammonium bromide (TBAB) at 75°C. Almost 100% biphenyl selectivity is obtained with iodobenzene. High coupling yields are achieved with 4-chlorotoluene and 4-chlorobenzaldehyde as the substrate. The competitive reduction reaction becomes predominant when the water-in-oil microemulsion is used as the solvent medium.

AB - Heterogeneous Pd/C-catalyzed reductive coupling of substituted haloarenes to the respective biaryls is effected with very high chemoselectivity in an oil-in-water microemulsion, using a reducing agent such as formate and a base, NaOH, in the presence of a catalytic amount of tetrabutylammonium bromide (TBAB) at 75°C. Almost 100% biphenyl selectivity is obtained with iodobenzene. High coupling yields are achieved with 4-chlorotoluene and 4-chlorobenzaldehyde as the substrate. The competitive reduction reaction becomes predominant when the water-in-oil microemulsion is used as the solvent medium.

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Highly chemoselective heterogeneous Pd-catalyzed biaryl synthesis from haloarenes: Reaction in an oil-in-water microemulsion

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