Halide effects on the Heck reaction in room temperature ionic liquids

Handy, Scott T.; Okello, Maurice

doi:10.1016/j.tetlet.2003.09.120

Cited by 35 publications

(18 citation statements)

References 8 publications

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“…After 2 hours, a Heck coupling with methyl acrylate was performed under conditions used previously in these labs and the reaction was allowed to proceed overnight. 8 Extraction with diethyl ether then afforded the clean Heck coupling product in 99% yield. 9 Anisole was also employed as the starting point for Heck couplings with two other, less-activated alkenes ( Table 1, entries 2 and 3).…”

Section: Methodsmentioning

confidence: 99%

One-Pot Halogenation-Heck Coupling Reactions in Ionic Liquids

Handy¹

2006

Synlett

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Traditional cross-coupling approaches rely upon two steps -halogenation and coupling -each of which is viewed and conducted independently. In an effort to develop a one-pot approach, we have noted that the halogenation and Heck coupling reactions can both be conducted in a room-temperature ionic liquid without the need to isolate the halogenated intermediate. Application to several systems shows that this approach works well for moderately to highly electron-rich aromatics.

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Section: Methodsmentioning

confidence: 99%

One-Pot Halogenation-Heck Coupling Reactions in Ionic Liquids

Handy¹

2006

Synlett

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“…It is thus clear that the anionic part of the phosphonium salt plays an important role: in contrast to chloride ions, bromide ions strongly enhance the catalytic activity. Such halide ion effects have already been observed, but are generally poorly understood, [59][60][61] except in some cases. [62] A possible explanation for the promoting role of nBu 4 PBr is outlined below (Scheme 3).…”

Section: Hydroamination Of Higher Alkenesmentioning

confidence: 98%

Platinum‐Catalyzed Intermolecular Hydroamination of Alkenes: Halide‐Anion‐Promoted Catalysis

2007

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Tetraalkylphosphonium halides play the role of “promoters” for the previously unknown PtII‐catalyzed hydroamination of alkenes. The promoting effect of these “cocatalysts” depends only upon their anionic moiety. The PtII/nBu4PBr system exhibits an unprecedented catalytic activity (aerobic conditions) for the hydroamination of ethylene and 1‐hexene (regioselectivity > 95 %, Markovnikov).(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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“…Furthermore, kinetic studies showed this IL to be less effective than the imidazolium-based one, such as [bmim]NTf 2 and [bmim]BF 4 . It was further shown that a catalytic amount of halides has an interesting accelerating effect on the reaction [235].…”

Section: Heck Reactionsmentioning

confidence: 99%