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Nuances in fundamental Suzuki−Miyaura cross-couplings employing [Pd(PPh3)4]: poor reactivity of aryl Iodides at lower temperatures

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Ho, CC ORCID: 0000-0002-7555-0635, Olding, A, Smith, JA ORCID: 0000-0001-6313-3298 and Bissember, AC ORCID: 0000-0001-5515-2878 2018 , 'Nuances in fundamental Suzuki−Miyaura cross-couplings employing [Pd(PPh3)4]: poor reactivity of aryl Iodides at lower temperatures' , Organometallics, vol. 37, no. 11 , pp. 1745-1750 , doi: 10.1021/acs.organomet.8b00189.

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Abstract

We have explored fundamental Pd-catalyzed Csp2− Csp2 Suzuki−Miyaura cross-couplings of aryl iodides (Ar−I)employing “classical” Pd/PPh3 catalyst systems. Surprisingly, we observed particularly inefficient couplings of these ostensibly reactive electrophiles in a range of conventional solvent mixtures at lower temperatures (∼50 °C), which was in stark contrast to analogous reactions featuring the equivalent aryl bromides. This feature of well-established Pd/PPh3-mediated Suzuki−Miyaura reactions has received scant attention in the literature. Most significantly, our studies suggest that the inefficient coupling of aryl iodides at lower temperatures derives from the unexpectedly poor turnover of the key on-cycle intermediate trans-[Pd(PPh3) 2(Ar)(I)] (or related PdII−I species) in the presence of PPh3.

Item Type: Article
Authors/Creators:Ho, CC and Olding, A and Smith, JA and Bissember, AC
Keywords: Suzuki–Miyaura, palladium cross-coupling, aryl iodides
Journal or Publication Title: Organometallics
Publisher: Amer Chemical Soc
ISSN: 0276-7333
DOI / ID Number: 10.1021/acs.organomet.8b00189
Copyright Information:

© 2018 American Chemical Society

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