Pd-catalyzed desulfonylative homocoupling of arenesulfonyl chlorides in the presence of hexamethyldisilane forming biaryls

Kashiwabara, Taigo; Tanaka, Masato

doi:10.1016/j.tetlet.2005.08.098

Cited by 37 publications

(25 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…To our delight, the mixture displayed an obvious effect to the cross-coupling reaction (69-75%) ( Table 1, entries 9-11) and solvent consisting of DMF and CH 3 CN (volume ratio 1:1) was shown to be best ( Table 1, entry 12). Finally, we adjusted the constitution of DMF and CH 3 CN in the range of 9:1 to 1:9 ( Table 1, entries [13][14][15][16][17][18][19][20]. A volume ratio of 1:4 (DMF vs. CH 3 CN) was chosen for the following optimization ( Table 1, entry 19).…”

Section: Resultsmentioning

confidence: 99%

“…Arylsulfonyl chlorides have been demonstrated as a class of electrophilic reagents in Pd‐catalyzed desulfitative C―C cross‐coupling reactions since then. Many types of coupling reaction, such as Negishi, Stille, Suzuki, Heck, Sonogashira, homocoupling and carbonylation have been well developed. However, it has not been extended to Pd‐catalyzed C―C bond formation with organosilanes (Hiyama cross‐coupling; Fig.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Pd‐catalyzed desulfitative Hiyama coupling with sulfonyl chlorides

Zhang

Liu

et al. 2014

Applied Organom Chemis

View full text Add to dashboard Cite

Palladium‐catalyzed desulfitative Hiyama cross‐coupling reactions of various arylsulfonyl chlorides with aryltriethoxysilane have been achieved in good yields. The reported cross‐coupling reactions are tolerant to the common functional groups regardless of electron‐withdrawing or electron‐donating, making these transformations attractive alternatives to the traditional cross‐coupling approaches. Copyright © 2014 John Wiley & Sons, Ltd.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Pd‐catalyzed desulfitative Hiyama coupling with sulfonyl chlorides

Zhang

Liu

et al. 2014

Applied Organom Chemis

View full text Add to dashboard Cite

show abstract

“…In 2005, Kashiwabara and Tanaka reported that the heating of benzenesulfonyl chlorides in the presence of 3 mol% Pd 2 (dba) 3 as the precatalyst and hexamethyldisilane also promoted desulfonylative homo-coupling (Scheme 14, b). 28 They performed the reaction with CuI, NaHCO 3 , Ag 2 CO 3 or Ag 2 O as oxidants and additives. With this procedure, para-meta-and also ortho-bromo-substituted benzenesulfonyl chlorides were successfully coupled affording products 25 in 65-96% yields.…”

Section: Homocouplingmentioning

confidence: 99%

Halo-substituted benzenesulfonyls and benzenesulfinates: convenient sources of arenes in metal-catalyzed C–C bond formation reactions for the straightforward access to halo-substituted arenes

Sasmal

Shi

et al. 2018

Org. Biomol. Chem.

View full text Add to dashboard Cite

Palladium-catalyzed reactions using aryl halides as one of the coupling partners represent a very popular method for generating carbon-carbon bonds. However, such couplings suffer from important limitations. As most palladium catalysts are very effective for the cleavage of C-halo bonds (Halo = Cl, Br or I), in many cases, the presence of several halide functional groups on arenes is not tolerated. Since two decades, and especially during the last few years, a new class of coupling partners, benzenesulfonyl and benzenesulfinate derivatives, has emerged as a powerful alternative to aryl halides for the Pd-catalyzed C-C bond formation, as the reactions performed with these substrates generally tolerate C-halo bonds. With these substrates, after a metal-catalyzed desulfitative coupling, a variety of halo-substituted arenes such as biaryls, styrenes, phenylacetylenes, acetophenones, benzonitriles… has been synthesized with high chemoselectivities. The use of these aryl sources allowed the synthesis of molecules containing several halo-substituents including iodo-substituents in only a few steps and provides very simple access to a very wide variety of halo-substituted arenes useful to materials chemists and also to biochemists. In this review, we will summarize the scope of the use of halo-substituted benzenesulfonyls and benzenesulfinates as coupling partners in metal-catalyzed C-C bond formation.

show abstract

“…Cross-coupling reactions of arylsulfonyl and sulfinate compounds have been well developed as an efficient synthetic method in recent years. [37,38] Arylsulfonyl chlorides, [39][40][41][42][43][44][45][46][47][48][49][50] arylsulfinates [51][52][53][54][55][56][57][58][59][60][61][62][63][64] and arylsulfonyl hydrazides [65][66][67][68][69][70][71] have been used as desulfonative/desulfitative arylation reagents in the synthesis of biaryls. Although arylsulfonyl chlorides are inexpensive and readily available compounds and have been used for many years in industry, they have not been extended to Pd-catalyzed carbon-carbon bond formation with organotrifluoroborates.…”

Section: Introductionmentioning

confidence: 99%

Desulfonative pd‐catalyzed coupling of aryl trifluoroborates with arylsulfonyl chlorides

Wei

Xue

Zhang³

et al. 2016

Applied Organom Chemis

View full text Add to dashboard Cite

A Pd‐catalyzed cross‐coupling of aryl trifluoroborates with arylsulfonyl chlorides has been successfully achieved. This transformation is a new method for the Suzuki–Miyaura‐type reaction of aryl trifluoroborates via the cleavage of C S bond, thus providing an alternative synthesis of biaryls. The reported cross‐coupling reactions are tolerant to many common functional groups regardless of electron‐donating or electron‐withdrawing nature, making these transformations attractive alternatives to the traditional Suzuki–Miyaura coupling approaches. Copyright © 2016 John Wiley & Sons, Ltd.

show abstract

Pd-catalyzed desulfonylative homocoupling of arenesulfonyl chlorides in the presence of hexamethyldisilane forming biaryls

Cited by 37 publications

References 38 publications

Pd‐catalyzed desulfitative Hiyama coupling with sulfonyl chlorides

Pd‐catalyzed desulfitative Hiyama coupling with sulfonyl chlorides

Halo-substituted benzenesulfonyls and benzenesulfinates: convenient sources of arenes in metal-catalyzed C–C bond formation reactions for the straightforward access to halo-substituted arenes

Desulfonative pd‐catalyzed coupling of aryl trifluoroborates with arylsulfonyl chlorides

Contact Info

Product

Resources

About