ChemInform Abstract: Palladium‐Catalyzed Vinylation of Arylsulfonyl Chlorides.

Kasahara, Akira; Izumi, Taeko; Kudou, N.; Azami, Hidenori; Yamamoto, Satoshi

doi:10.1002/chin.198821160

Cited by 7 publications

(7 citation statements)

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“…Palladium‐catalyzed desulfitative Mizoroki–Heck‐type coupling with sulfonyl chlorides : In continuation of work by Kasahara9a,b and Miura 9c,d and their respective co‐workers, we investigated whether catalysts other than [PdCl 2 (PhCN) 2 ], Pd(OAc) 2 , PdCl 2 , Pd black, and [PdCl 2 (PPh 3 ) 2 ] would improve the yield of the desulfitative vinylations. Our exploratory experiments started with the coupling of 1‐naphthalenesulfonyl chloride ( 1 ; 2 mmol) and butyl acrylate ( 2 ; 5.5 mmol) in the presence of [PdCl 2 (PhCN) 2 ] (3 mol %), Me(oct) 3 NCl (15 mol %), and K 2 CO 3 (4 mmol) in m ‐xylene.…”

Section: Resultsmentioning

confidence: 99%

Palladium‐Catalyzed Desulfitative Mizoroki–Heck Couplings of Sulfonyl Chlorides with Mono‐ and Disubstituted Olefins: Rhodium‐Catalyzed Desulfitative Heck‐Type Reactions under Phosphine‐ and Base‐Free Conditions

Dubbaka

Vogel

2005

Chemistry A European J

122

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New conditions have been found for the desulfitative Mizoroki-Heck arylation and trifluoromethylation of mono- and disubustituted olefins with arenesulfonyl and trifluoromethanesulfonyl chlorides. Thus (E)-1,2-disubstituted alkenes with high stereoselectivity and 1,1,2-disubstituted alkenes with 12:1 to 21:1 E/Z steroselectivity can be obtained. Herrmann's palladacycle at 0.1 mol % is sufficient to catalyze these reactions, for which electron-rich or electron-poor sulfonyl chlorides and alkenes are suitable. If phosphine- and base-free conditions are required, 1 mol % [RhCl(C(2)H(4))(2)] catalyzes the desulfitative cross-coupling reactions. Contrary to results reported for [RuCl(2)(PPh(3))(2)]-catalyzed coupling reactions with sulfonyl chlorides, the palladium and rhodium desulfitative Mizoroki-Heck coupling reactions are not inhibited by radical scavenging agents. Possible sulfones arising from the sulfonylation of alkenes at 60 degrees C are not desulfitated at higher temperatures in the presence of the Pd or Rh catalysts.

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Section: Resultsmentioning

confidence: 99%

Palladium‐Catalyzed Desulfitative Mizoroki–Heck Couplings of Sulfonyl Chlorides with Mono‐ and Disubstituted Olefins: Rhodium‐Catalyzed Desulfitative Heck‐Type Reactions under Phosphine‐ and Base‐Free Conditions

Dubbaka

Vogel

2005

Chemistry A European J

122

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“…In 1988, Kasahara reported palladium-catalyzed Mizoroki-Heck-type desulfitative alkenylation of arylsulfonyl chlorides with styrene and electron-deficient monosubstituted alkenes (Scheme 44) [96].…”

Section: Cross-coupling Reaction Of Sulfonyl Chloridesmentioning

confidence: 99%

C–S Bond Activation

2018

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“…They have been used for more than a century in material sciences and medicinal chemistry. [18][19][20][21][22][23] Recently, we have shown that Stille, carbonylative Stille, 24,25 Suzuki-Miyaura, 26 Sonogashira-Hagihara 27 type cross-couplings and Mizoroki-Heck 28,29 type arylations can be carried out using sulfonyl chlorides as electrophilic partners under desulfinylation conditions. 30 In the case of Mizoroki-Heck coupling reaction, Pd nanoparticles in nitrile-functionalized ionic liquid, without expensive or toxic ligands can be used as recoverable catalyst.…”

Section: Introductionmentioning

confidence: 99%

Palladium-catalyzed desulfinylative C–C allylation of Grignard reagents and enolates using allylsulfonyl chlorides and esters

Volla¹,

Dubbaka²,

Vogel³

2009

Tetrahedron

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a b s t r a c t 2-Methylprop-2-ene-, prop-2-ene-, 1-methylprop-2-ene-, and (E)-but-2-enesulfonyl chlorides have been used as electrophilic partners in desulfinylative palladium-catalyzed C-C coupling with Grignard reagents and sodium salts of dimethyl malonate and methyl acetoacetate. Neopentyl alk-2-ene sulfonates can also be used as electrophilic partners in desulfinylative allylic arylations and allylic alkylations. The regioselectivity of the allylic arylation and alkylation depends on the nature of the catalyst. With PdCl 2 (PhCN) 2 , (E)-crotyl derivatives are formed in high regioselectivity using either 1-methylprop-2-eneor (E)-but-2-enesulfonyl chloride.

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ChemInform Abstract: Palladium‐Catalyzed Vinylation of Arylsulfonyl Chlorides.

Abstract: ChemInform Abstract Palladium-catalyzed reaction of the arylsulfonyl chlorides (I) with the activated olefins (II) in the presence of N-ethylmorpholine yields the styrenes (III) and the diaryl disulfides (IV).

Cited by 7 publications

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Palladium‐Catalyzed Desulfitative Mizoroki–Heck Couplings of Sulfonyl Chlorides with Mono‐ and Disubstituted Olefins: Rhodium‐Catalyzed Desulfitative Heck‐Type Reactions under Phosphine‐ and Base‐Free Conditions

Palladium‐Catalyzed Desulfitative Mizoroki–Heck Couplings of Sulfonyl Chlorides with Mono‐ and Disubstituted Olefins: Rhodium‐Catalyzed Desulfitative Heck‐Type Reactions under Phosphine‐ and Base‐Free Conditions

C–S Bond Activation

Palladium-catalyzed desulfinylative C–C allylation of Grignard reagents and enolates using allylsulfonyl chlorides and esters

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