- Palladium-catalyzed alkoxycarbonylation of aryl p-toluenesulfonate
-
Methyl- and ethyl arylcarboxylates were synthesized by palladium-catalyzed alkoxycarbonylation of various aryl p-toluenesulfonates (tosylates). Yields were highly dependent on the substituent of aryl tosylates and phosphine ligands used. Ethoxycarbonylation of 4-acetylphenyl tosylate by the use of a bisphosphine ligand gave ethyl 4-acetylbenzoate in quite satisfactory yields.
- Kubota, Yoshihiro,Nakada, Shigekuni,Sugi, Yoshihiro
-
-
Read Online
- The Synthesis and Catalytic Activity of New Mixed NHC-Phosphite Nickel(0) Complexes
-
Herein we describe the synthesis and isolation of the first low-valent NHC-phosphite nickel complexes of general formula Ni(NHC)[P(OAr)3]2. These three-coordinate Ni(0) compounds were fully characterized, including by X-ray crystallography that highlighted their trigonal planar geometry. The representative complex Ni(IMes)[P(OPh)3]2 was used to show that a phosphite ligand is readily substituted in the presence of an aldehyde or nitrile. These stoichiometric studies then led to an investigation of their catalytic properties in the Suzuki-Miyaura cross-coupling reactions between aryl tosylates and aryl boronic acids, a first for such a NHC-Ni catalyst. Finally, mechanistic investigations led to the isolation of a well-defined oxidative addition product.
- Dorta, Reto,Duczynski, Jeremy,Moggach, Stephen A.,Sobolev, Alexandre N.,Stewart, Scott G.
-
supporting information
(2020/01/21)
-
- Palladium-Catalyzed Cyclobutanation of Aryl Sulfonates through both C-O and C-H Cleavage
-
A palladium-catalyzed cyclobutanation of aryl sulfonates with strained alkenes has been developed. The methodology is featured to achieve the cleavage of both C-O and C-H bonds of phenol derivatives in one pot. Under the reaction conditions, in addition t
- Zhang, Liangwei,Liu, Long,Huang, Tianzeng,Dong, Qizhi,Chen, Tieqiao,Chen, Tieqiao
-
p. 2189 - 2196
(2020/06/05)
-
- Copper-Catalyzed Regioselective C-H Sulfonyloxylation of Electron-Rich Arenes with p-Toluenesulfonic Acid and Sulfonyloxylation of Aryl(mesityl)iodonium Sulfonates
-
Copper-catalyzed regioselective C-H sulfonyloxylation of electron-rich arenes with p-toluenesulfonic acid has been developed. Electron-rich benzene derivatives and heteroarenes can undergo this C-H sulfonyloxylation reaction to generate aryl tosylates. Furthermore, sulfonyloxylation of aryl(mesityl)iodonium sulfonates has also been investigated. Both aryl(mesityl)iodonium tosylates and triflates can react smoothly to get aryl sulfonates. The formed aryl sulfonates can be converted to phenols, as well as used as good partners of cross-coupling reactions.
- Huang, He,Wu, Yang,Zhang, Wen,Feng, Chun,Wang, Bi-Qin,Cai, Wan-Fei,Hu, Ping,Zhao, Ke-Qing,Xiang, Shi-Kai
-
p. 3094 - 3101
(2017/03/23)
-
- Copper-Mediated Functionalization of Aryl Trifluoroborates
-
This paper describes the Cu(OTf)2-mediated coupling of aryl and heteroaryl trifluoroborates with tetrabutylammonium or alkali metal salts to form C-O, C-N, and C-halogen bonds. The reactions proceed under mild conditions (often room temperature over 16 hours) with carboxylate, halide, and azide salts, all nucleophiles that have been underrepresented in the copper cross-coupling literature. Preliminary results show that copper salts bearing weakly coordinating X-type ligands are essential for enabling these transformations to proceed under mild conditions.
- Schimler, Sydonie D.,Sanford, Melanie S.
-
supporting information
p. 2279 - 2284
(2016/10/06)
-
- Direct Carboxylation of Aryl Tosylates by CO2 Catalyzed by in situ-Generated Ni0
-
A novel Ni0-catalyzed carboxylation of aryl tosylates with carbon dioxide has been achieved under moderate temperatures and atmospheric pressure. In this procedure, the active Ni0 species is generated in situ by simply mixing the Ni0 precatalyst [NiBr2(bipy)] with an excess of manganese metal. This approach requires neither a glove-box nor the tedious preparation of sophisticated intermediate organometallic derivatives. This mild, convenient, and user-friendly process is successfully applied to the valorization of carbon dioxide and the synthesis of versatile reactants with broad tolerance of substituents.
- Rebih, Fatima,Andreini, Manuel,Moncomble, Aurlien,Harrison-Marchand, Anne,Maddaluno, Jacques,Durandetti, Muriel
-
supporting information
p. 3758 - 3763
(2016/03/08)
-
- Dimerization of Aryl Sulfonates by in situ Generated Nickel(0)
-
A mild and user-friendly nickel-catalyzed method for the reductive homocoupling of aromatic tosylates is presented. The reaction proceeds between room temperature and 60 °C, with stable substrates (ArOTs) easily prepared from inexpensive and commercially available phenols or naphthols. It relies on a catalytic amount (10 mol%) of a robust catalyst (NiBr2bipy) that does not require the preparation of sensitive organometallic intermediates. Yields are good to excellent.
- Maddaluno, Jacques,Durandetti, Muriel
-
supporting information
p. 2385 - 2388
(2015/10/19)
-
- Iron-catalyzed coupling of aryl sulfamates and aryl/vinyl tosylates with aryl grignards
-
The iron-catalyzed coupling of aryl sulfamates and tosylates with aryl Grignard reagents is reported for the first time. The methodology employs air-stable, low-cost FeF3·3H2O and the N-heterocyclic carbene ligand IPr·HCl as the preligand to form a long-lived catalyst upon treatment with aryl Grignards. The reaction provides a range of cross-coupled products in good-to-excellent yields. In contrast to previous reports with aryl chlorides, these reactions proceed with low levels of Grignard homocoupling regardless of the iron source.
- Agrawal, Toolika,Cook, Silas P.
-
supporting information
p. 5080 - 5083
(2014/12/11)
-
- Suzuki-Miyaura coupling of aryl sulfonates with arylboronic acids using a morpholine-Pd(OAc)2 catalyst system
-
We report a new catalyst system, a morpholine-Pd(OAc)2 complex, for Suzuki-Miyaura coupling of aryl tosylates or mesylates with arylboronic acids to give biaryl compounds. The morpholine-Pd(OAc)2 catalyst system is proposed to be a precursor of the catalytically active species in the coupling reaction. Aryl chlorides and aryl triflates can also be used in this coupling reaction. Altogether, 22 biaryl compounds were obtained using this catalyst system. We report a new catalyst system, a morpholine-Pd(OAc) 2 complex, for Suzuki-Miyaura coupling of aryl tosylates or mesylates with arylboronic acids to give biaryl compounds. The morpholine-Pd(OAc) 2 catalyst system is proposed to be a precursor of the catalytically active species in the coupling reaction. Copyright
- Abe, Taichi,Mino, Takashi,Watanabe, Kohei,Yagishita, Fumitoshi,Sakamoto, Masami
-
p. 3909 - 3916
(2014/06/24)
-
- Copper-catalysed coupling of aryl tosylates with sodium arylsulfinates
-
Diaryl sulfones derivatives were easily synthesised from aryl tosylates and sodium arylsulfinates in high yields using [Cu(CH3CN)4]PF6 as catalyst. The transformation is efficient, simple and the starting materials are readily available.
- Wang, Chunjie,Zhang, Hui,Li, Zhiwei,Wang, Ziyun
-
p. 639 - 642
(2015/02/02)
-
- Cs2CO3 catalyzed rapid and efficient conversion of amines into sulfonamides; Alcohols and phenols into sulfonic esters
-
A simple and efficient method has been developed for the sulfonylation of several amines, alcohols, and phenols by p-toluenesulphonylchloride (p-TsCl) in the presence of catalytic amount of Cs2CO3 at 25C to obtain sulfonamides and sulfonic esters in very good yields. Cs2CO3 has been found to be highly efficient catalyst. Taylor & Francis Group, LLC.
- Reddy, M. B. Madhusudana,Pasha
-
experimental part
p. 1867 - 1875
(2011/10/11)
-
- Decarboxylative cross-coupling of aryl tosylates with aromatic carboxylate salts
-
(Figure Presented) A bimetallic copper/palladium catalyst system is disclosed that enables the use of tosylates as carbon electrophiles in decarboxylative coupling reactions. A variety of aromatic carboxylate salts, regardless of their substitution pattern, have been coupled with these inexpensive and readily available electrophiles to give the corresponding biaryl compounds in good yields (see scheme).
- Goossen, Luksa J.,Rodriguez, Nuria,Lange, Paul P.,Linder, Christophe
-
supporting information; experimental part
p. 1111 - 1114
(2010/04/29)
-
- Unusual Reaction of Azoxybenzenes with p-Toluenesulfonic Acid in Acetic Anhydride
-
Treatment of azoxybenzene with p-toluenesulfonic acid in acetic anhydride gave tosylates of 4- and 2-(phenylazo)phenols, and the corresponding acetates as by-product, besides azobenzene.However, a similar reaction of 4,4'-difluoroazoxybenzene gave 2-tosyloxy-4,4'-difluoroazobenzene as rearrangement product, besides 4-fluorophenyl tosylate and 4-fluorophenyl acetate.Meanwhile, the reaction of 4,4'-diacetoxyazoxybenzene afforded 4-acetoxyphenyl tosylate and hydroquinone diacetate in high yields.These unique reactions involve C-N bond cleavage, and may proceed through a pathway involving formation of benzenediazonium ion as the key intermediate.
- Shimao, Ichiro,Fujimori, Ken,Oae, Shigeru
-
p. 1538 - 1542
(2007/10/02)
-