- Synthesis of aryl thioethers through the N -chlorosuccinimide-promoted cross-coupling reaction of thiols with Grignard reagents
-
A convenient one-pot approach for the synthesis of aryl sulfides through the coupling of thiols with Grignard reagents in the presence of N-chlorosuccinimide is described. The sulfenylchlorides were formed when thiols were treated with N-chlorosuccinimide, and the resulting sulfenylchlorides were then directly reacted with Grignard reagents to provide aryl sulfides in good to excellent yields under mild reaction conditions. Functional groups including ester, fluoro, and chloro are tolerated by the reaction conditions employed. It is important to note that this method has a short reaction time (30 min in total) and represents an alternative approach for the synthesis of aryl sulfides over the existing protocols.
- Cheng, Jun-Hao,Ramesh, Chintakunta,Kao, Hsin-Lun,Wang, Yu-Jen,Chan, Chien-Ching,Lee, Chin-Fa
-
p. 10369 - 10374
(2013/01/15)
-
- A general, efficient, and functional-group-tolerant catalyst system for the palladium-catalyzed thioetherification of aryl bromides and iodides
-
The cross-coupling reaction of aryl bromides and iodides with aliphatic and aromatic thiols catalyzed by palladium complexes of the bisphosphine ligand CyPF-tBu (1) is reported. Reactions occur in excellent yields, broad scope, high tolerance of functional groups, and with turnover numbers that exceed those of previous catalysts by 2 or 3 orders of magnitude. These couplings of bromo- and iodoarenes are more efficient than the corresponding reactions of chloroarenes and could be conducted with less catalyst loading and/or milder reaction conditions. Consequently, limitations regarding scope and functional group tolerance previously reported in the coupling of aryl chlorides are now overcome.
- Fernandez-Rodriguez, Manuel A.,Hartwig, John F.
-
experimental part
p. 1664 - 1672
(2009/07/17)
-
- Iron-catalyzed thioetherification of thiols with aryl iodides
-
FeCl3 in combination with bisphosphine ligands represents an efficient catalyst system for the cross-coupling of aryl- and alkyl thiols with aryl iodides, a broad spectrum of functional groups can be tolerated during the catalysis. The Royal Society of Chemistry 2009.
- Wu, Jhih-Ru,Lin, Che-Hung,Lee, Chin-Fa
-
supporting information; experimental part
p. 4450 - 4452
(2009/12/29)
-
- CATALYSTS FOR ARYL SULFIDE SYNTHESIS AND METHOD OF PRODUCING ARYL SULFIDES
-
The present invention relates to the formation of aryl sulfides and aryl thiols from aryl halides and thiols, thiolates or thiolate equivalents. The present invention provides a catalyst for the coupling of aryl halides with alkyl or aryl thiols or a hydrogen sulfide equivalent to form aryl alkyl, aryl silyl or diaryl sulfides. The reaction encompasses bromoarenes and other similar compounds containing leaving groups as well as nitrile, ester, keto, free hydroxyl, free amino, free carboxylic acid and other common functionalities. The invention can be used to prepare pharmaceutical compounds, especially including their intermediates, agricultural agents and aryl sulfide polymers.
- -
-
Page/Page column 20; 33
(2008/06/13)
-
- Highly efficient and functional-group-tolerant catalysts for the palladium-catalyzed coupling of aryl chlorides with thiols
-
The cross-coupling reaction of aryl chlorides with aliphatic and aromatic thiols catalyzed by palladium complexes of the strongly binding bisphosphine CyPF-tBu ligand (1) is reported. Most of the reactions catalyzed by complexes of ligand 1 occur with turnover numbers that exceed those of previous catalysts by two orders of magnitude. The reactions occur with excellent yields, broad scope and high tolerance of functional groups. Coupling of aryl halides with thiols in the presence of low loadings of catalysts derived from other Josiphos type ligands, as well as ligands of other structural types, are also described.
- Fernandez-Rodriguez, Manuel A.,Shen, Qilong,Hartwig, John F.
-
p. 7782 - 7796
(2007/10/03)
-
- Chiral organometallic compounds
-
A chiral, organometallic compound which, at a molecular level, has no C2 symmetry and comprises a carbon to carbon bond joining a chiral carbon atom to a carbon atom of a cyclopentadiene ring that is non-symmetrically substituted. Examples of such compounds include compounds of formula (I): STR1 wherein X1 and X2 are, independently, groups which are removable during a chemical reaction; M is titanium, zirconium or hafnium; and R1-8,11 are as specified in the description.
- -
-
-
- Lewis Acid Induced Nucleophilic Substitution Reaction of β-Nitro Sulfides
-
The nitro group of β-nitro sulfides is readily substituted by an allyl or a cyano group or hydrogen on treatment with allyltrimethylsilane, cyanotrimethylsilane, or triethylsilane in the presence of an appropriate Lewis acid.The intramolecular Friedel-Cra
- Kamimura, Akio,Sasatani, Hiroyuki,Hashimoto, Toshihiro,Ono, Noboru
-
p. 4998 - 5003
(2007/10/02)
-
- IONIC DENITROHYDROGENATION OF α-NITRO OR β-NITRO SULFIDES WITH TRIETHYLSILANE
-
The nitro groups of α-nitro or β-nitro sulfides are replaced by hydrogen on treatment with triethylsilane in the presence of Lewis acid.
- Ono, Noboru,Hashimoto, Toshihiro,Jun, Tuo Xiao,Kaji, Aritsune
-
p. 2277 - 2280
(2007/10/02)
-