Nickel-Catalyzed Suzuki–Miyaura

  • Author: ChemViews
  • Published Date: 07 February 2011
  • Source / Publisher: European Journal of Organic Chemistry/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Nickel-Catalyzed Suzuki–Miyaura

Related Societies

Transition-metal-catalyzed Suzuki–Miyaura reactions are an important and powerful tool for the construction of biaryl motifs commonly found in natural products, pharmaceuticals, and chemical materials. Although palladium catalysts have dominated these transformations over the past decades, efforts to explore other metal alternatives have been attracting considerable interest.

In this regard, the nickel-catalyzed Suzuki–Miyaura reactions perform excellently. The advantages of catalyst systems with nickel over those with palladium are mainly their low cost and high reactivity toward challenging substrates (e.g., deactivated aryl chlorides and sulfonates) without the need of special ligands.

Room-temperature transformations also represent a highly desirable process from a synthetic point of view. Xin-Heng Fan and Lian-Ming Yang, Chinese Academy of Sciences, have reported the room-temperature Suzuki–Miyaura aryl–aryl cross-coupling. This was achieved by using an easily-accessible, air-stable NiII–(σ-aryl) complex as precatalyst without the aid of any organometallic reagent or external reductant. The NiII complex, in conjunction with some phosphane ligands, was able to efficiently cross-couple aryl sulfonates (OTs, OMs) and/or halides (Cl, Br, I) with arylboronic acids at room temperature in toluene/water in the presence of K2CO3 as base.

This facile, mild, and general protocol represents a new advance in Suzuki cross-coupling reactions.

Images: (c) Wiley-VCH

Article Views: 5248

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

If you would like to reuse any content, in print or online, from, please contact us first for permission. more

CONNECT: on Facebook on Twitter on YouTube on LinkedIn Sign up for our free newsletter

Magazine of Chemistry Europe (16 European Chemical Societies)published by Wiley-VCH