Preparation of unsymmetrical terphenyls via the nickel-catalyzed cross-coupling of alkyl biphenylsulfonates with aryl Grignard reagents

Cho, Chul‐Hee; Kim, Insook; Park, Kwangyong

doi:10.1016/j.tet.2004.03.072

Cited by 43 publications

(29 citation statements)

References 72 publications

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“…41 Pd-catalyzed Heck coupling of bromo-BR with methoxy-substituted phenylenevinylene dimethyl aniline molecular wire 4 available in 3 steps according to established procedures 23 provided BeRST 1 in 62% yield, after purification on silica gel. BeRST 1 exhibits spectral properties similar to the parent BR dye, with excitation and emission centered at 658 nm and 683 nm (Fig.…”

Section: Resultsmentioning

confidence: 99%

A Photostable Silicon Rhodamine Platform for Optical Voltage Sensing

2015

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This paper describes the design and synthesis of a photostable, far-red to near-infrared (NIR) platform for optical voltage sensing. We developed a new, sulfonated silicon rhodamine fluorophore and integrated it with a phenylenevinylene molecular wire to create a Berkeley Red Sensor of Transmembrane potential, or BeRST 1 (“burst”). BeRST 1 is the first member of a class of farred to NIR voltage sensitive dyes that make use of a photoinduced electron transfer (PeT) trigger for optical interrogation of membrane voltage. We show that BeRST 1 displays bright, membrane-localized fluorescence in living cells, high photostability, and excellent voltage sensitivity in neurons. Depolarization of the plasma membrane results in rapid fluorescence increases (24% ΔF/F per 100 mV). BeRST 1 can be used in conjunction with fluorescent stains for organelles, Ca2+ indicators, and voltage-sensitive fluorescent proteins. In addition, the red-shifted spectral profile of BeRST 1, relative to commonly employed optogenetic actuators like ChannelRhodopsin2 (ChR2), which require blue light, enables optical electrophysiology in neurons. The high speed, sensitivity, photostability and long-wavelength fluorescence profiles of BeRST 1 make it a useful platform for the non-invasive, optical dissection of neuronal activity.

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Section: Resultsmentioning

confidence: 99%

A Photostable Silicon Rhodamine Platform for Optical Voltage Sensing

2015

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“…29 We have also shown that aliphatic sulfonyl chlorides are also excellent electrophiles. 31 Among the earliest, most economical and useful nucleophilic partners are the Grignard reagents, which can be coupled with all kinds of electrophilic partners such as sulfides, [32][33][34][35][36][37][38][39] sulfoxides 32,40 sulfoximines, [41][42][43][44][45] sulfones, 46-52 sulfonic esters, [53][54][55] and sulfonamides 56 in the presence of nickel catalysts.…”

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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“…52 Using different transmetallating reagents, the Corriu-Kumada reaction was combined with the SM reaction to furnish unsymmetrical o-, m-and p-terphenyls from neopentyl bromobenzenesulfonates (Scheme 13, equation 3). 53 The procedure first utilized a Suzuki protocol for the biaryl formation, which occurred selectively at the bromide. This was followed by a nickel-catalyzed coupling with the Grignard reagent.…”

Section: Scheme 13mentioning

confidence: 99%