Nickel‐Catalyzed Suzuki–Miyaura Coupling of a Tertiary Iodocyclopropane with Wide Boronic Acid Substrate Scope: Coupling Reaction Outcome Depends on Radical Species Stability. Issue 5 (13th March 2015)

• Record Type: Journal Article
• Authors: Yotsuji, Keisuke; Hoshiya, Naoyuki; Kobayashi, Takaaki; Fukuda, Hayato; Abe, Hiroshi; Arisawa, Mitsuhiro; Shuto, Satoshi
• Is Part Of: Advanced synthesis & catalysis. Volume 357:Issue 5(2015)
• Page Start: 1022
• Page End: 1028
• Publication Date: 2015-03-13
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201401000
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>We describe a nickel‐catalyzed Suzuki–Miyaura arylation of a tertiary iodocyclopropane with arylboronic acids; this is an efficient and convergent strategy for providing various enantioenriched arylcyclopropanes with a quaternary stereogenic center. This is the first metal‐catalyzed coupling between a tertiary alkyl electrophile and a wide range of aromatics, including heteroaromatics. We found that the outcome of the Ni‐catalyzed coupling with halides as electrophiles was dependent on the stability of the radical species formed during the reaction. The use of <italic>tert‐</italic>butyl alcohol (<italic>t</italic>‐BuOH) as the reaction solvent was very effective, because of its stability under the radical‐generating reaction conditions.</p> <p> <boxed-text content-type="graphic" position="anchor" orientation="portrait"> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgjbsh6k4z" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </boxed-text> </p> </abstract>