156098-13-4Relevant academic research and scientific papers
POTASSIUM TRIISOPROPYLSILANETHIOLATE: VINYL AND ARYL SULFIDES THROUGH Pd-CATALYZED CROSS COUPLING
Rane, Anil M.,Miranda, Edgar I.,Soderquist, John A.
, p. 3225 - 3226 (1994)
Vinyl and aryl halides are efficiently converted, under Pd catalysis, with KSTIPS (1) to the corresponding silyl sulfides (2, 3).The naphthyl derivative was easily hydrolyzed to the mercaptan 4, or alkylated or alkenylated to provide unsymmetrical sulfides (5, 6).
Palladium-Catalyzed Carbothiolation via Trapping of the σ-Alkyl Palladium Intermediate with RSTIPS
Hosoya, Yosuke,Kobayashi, Ikumi,Mizoguchi, Kota,Nakada, Masahisa
supporting information, p. 8280 - 8284 (2019/10/14)
A palladium-catalyzed carbothiolation via the reaction of a σ-alkyl palladium intermediate with a TIPS thioether is described. It was found that the use of Cs2CO3, (IPr)Pd(allyl)Cl, and a TIPS thioether was key to obtaining alkyl aryl and dialkyl sulfides in high yield through the reaction of a σ-alkyl palladium intermediate. The developed reaction is applicable to a wide range of substrates and thiols.
Synthesis of 3-substituted 2-cyclohexenones through umpoled functionalization
Lechuga-Eduardo, Harim,Zarza-Acu?a, Eduardo,Romero-Ortega, Moisés
, p. 3234 - 3237 (2017/07/27)
A new protocol to obtain 3-substituted 2-cyclohexenones, was developed by reversing the chemical reactivity of 2-cyclohexenone. One-pot synthesis of 3-substituted 2-cyclohexenones can be achieved by treatment of 3-phenylthiosilyl enol ether with a mixture of t-BuLi/HMPA that allows hydrogen-selective exchange in presence of reactive electrophiles such as aldehydes, ketones and alkyl halides. This affords the corresponding product in moderate overall yield, after silyl enol ether cleavage and concomitant thiophenol elimination initiated with TBAF.
One-pot synthesis of unsymmetrical diaryl thioethers by palladium-catalyzed coupling of two aryl bromides and a thiol surrogate
Fernandez-Rodriguez, Manuel A.,Hartwig, John F.
supporting information; experimental part, p. 2355 - 2359 (2010/07/02)
Extraordinarily simple, convenient, and efficient: A general and operationally simple one-pot synthesis of unsymmetrical diaryl sulfides by coupling two different bromoarenes and triisopropylsilanethiol (TIPS-SH) is reported. This protocol overcomes the narrow availability of arene thiols and their instability to oxidation. These reactions catalyzed by palladium complexes generated from the alkylbisphosphine CyPF-tBu occur in good to excellent yields with wide scope and high tolerance of functional groups.
A general and long-lived catalyst for the palladium-catalyzed coupling of aryl halides with thiols
Fernandez-Rodriguez, Manuel A.,Shen, Qilong,Hartwig, John F.
, p. 2180 - 2181 (2007/10/03)
A general catalytic system for the coupling of aryl halides and sulfonates with thiols based on the use of the CyPF-t-Bu ligand (1) is reported. The reactions catalyzed by complexes of 1 occur in excellent yields with broad scope and exhibit extraordinary turnover numbers and high tolerance of functional groups. Turnover numbers usually exceed those of previous catalysts by 2 or 3 orders of magnitude. In addition, the reactions of aryl tosylates with alkane thiols to form aryl sulfides are reported for the first time. Finally, the synthesis of a diarylsulfide from two bromoarenes was accomplished using a hydrogen sulfide surrogate. Copyright
