Nickel-Catalyzed Cross-Coupling of Neopentyl Arenesulfonates with Methyl and Primary Alkylmagnesium Bromides

Cho, Chul‐Hee; Sun, Myungchul; Seo, Yong-Seok; Kim, Chul-Bae; Park, Kwangyong

doi:10.1021/jo048300c

Cited by 30 publications

(7 citation statements)

References 29 publications

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“…Nickel catalyzed coupling of a variety of aromatic chlorides and fluorides with Grignard reagents [95,96]. Neopentyl arenesulfonates were used in place of aryl halides in cross-coupling reaction with alkyl magnesium bromides [97]. Nickel catalyzed couplings of aryl O-sulfamates with Grignard reagents [98,99].…”

Section: Carbon-carbon Bond-forming Reactions Via Transmetallationmentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

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Section: Carbon-carbon Bond-forming Reactions Via Transmetallationmentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

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“…Carbon-carbon bond formation can also be achieved following activation of carbon-sulfur or carbon-oxygen bonds, even though higher temperatures and higher catalyst loadings are generally required [36]. Heteroaromatic alkyl disulfides and thioethers like the quinoxaline 171 [105] or neopentylarene sulfonates such as 173 [106] can be alkylated in high yields (Scheme 5.37). Interestingly, the alkyloxysulfonyl group is not displaced by palladium catalysts.…”

Section: Cross-coupling With C(sp 2 )-Electrophilesmentioning

confidence: 99%

“…The organic layer was washed with 1% aqueous HCl, water, and brine, then dried over MgSO 4 and concentrated in vacuo. The crude compound was purified by column chromatography (ethyl acetate/n-hexane 1 : 10) to give 43.9 mg (79%) of 174 as a yellow oil (Scheme 5.37) [106]. …”

Section: Nn-5-trimethylnaphthalen-1-amine (174)mentioning

confidence: 99%

Carbon–Carbon‐Bond‐Forming Reactions Mediated by Organomagnesium Reagents

Chemla

Ferreira

Pérez‐Luna

et al. 2013

Metal‐Catalyzed Cross‐Coupling Reactions and More

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IntroductionFirst reported at the beginning of the twentieth century [1], organomagnesiums are very important synthetic tools. In the field of coupling reactions, first examples of transition-metal-mediated reactions have been reported by Gilman and Lichtenwalter [2] with the oxidative homo-coupling of aryl Grignard reagents in the presence of transition metal halides as both catalyst precursors and oxidants. This reaction was later greatly improved by Kharasch [3], who showed that an efficient homo-coupling reaction could be observed with a small amount of CoCl 2 (3 mol%) and an organic halide as a stoichiometric oxidant. This breakthrough was then followed by the report in 1941 on cross-coupling reactions of arylmagnesium bromides with vinylic halides in the presence of various transition metal salts by the same group [4]. Surprisingly, this seminal work remained mainly unexploited, until this reaction was reinvestigated by several groups in the beginning of the 1970s [5]. Thus, Kochi and Tamura [6, 7] described in 1971 the use of Fe(III) salts as catalyst precursors for cross-coupling reactions, while Kumada [8] and Corriu [9] reported the use of nickel for similar transformations [10,11]. At the same time, the group of Normant [12] described the Cu-catalyzed reaction of the Grignard reagents with organic halides, followed by the report of Murahashi [13] on the use of palladium as a catalyst in similar cross-couplings. Most cross-coupling reactions have been performed with unfunctionalized Grignard reagents because no general method for preparing oligofunctional organomagnesium reagents was available. However, the situation is rapidly evolving, thanks to the groundbreaking work of Knochel and coworkers [14] on the preparation of highly functionalized Grignard reagents. In this chapter, the scope and limitations of cross-coupling reactions involving organomagnesium reagents are showcased with select examples from the recent literature with a special focus on functional-group-tolerant procedures. The recent developments of the most challenging transformations including either the use of oligofunctional metallic species or β-hydrogen-containing nucleophiles will be specially highlighted.

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“…Sulfonates are useful partners in C-C coupling reactions [13] of organolithium [8], -copper [14][15][16] and -zinc reagents [17][18][19] (Scheme 1, pathway a). Grignard reagents can react either by C-O bond cleavage [7,[20][21][22] or C-S bond cleavage [23][24][25] (Scheme 1, pathway a and pathway b, respectively) to give C-C coupling products. Organolithiums [10] and Grignard reagents [11,12] are also known to react with arenesulfonates to give C-S coupling leading to the formation of sulfones by S-O bond cleavage (Scheme 1, pathway c).…”

Section: Introductionmentioning

confidence: 99%