68004-04-6Relevant articles and documents
Cu-Catalyzed Aerobic Oxidative Sulfuration/Annulation Approach to Thiazoles via Multiple Csp3-H Bond Cleavage
Wang, Xiaoyang,Qiu, Xu,Wei, Jialiang,Liu, Jianzhong,Song, Song,Wang, Wen,Jiao, Ning
supporting information, p. 2632 - 2636 (2018/05/22)
A novel and practical Cu-catalyzed aerobic oxidative synthesis of thiazoles was developed. This chemistry for the first time achieved thiazole construction from simple aldehydes, amines, and element sulfur through multiple Csp3-H bond cleavage processes. Molecular oxygen was used as a green oxidant in this oxidative protocol. The substrate scope is broad with the tolerance of aliphatic amines. The mechanistic study might promote the reaction design for a new sulfuration/annulation reaction with readily available element sulfur.
Facile Synthesis of 2,5-Disubstituted Thiazoles from Terminal Alkynes, Sulfonyl Azides, and Thionoesters
Miura, Tomoya,Funakoshi, Yuuta,Fujimoto, Yoshikazu,Nakahashi, Junki,Murakami, Masahiro
, p. 2454 - 2457 (2015/05/27)
A sequential procedure for the synthesis of 2,5-disubstituted thiazoles from terminal alkynes, sulfonyl azides, and thionoesters is reported. A copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes with sulfonyl azides affords 1-sulfonyl-1,2,3-triazoles, which then react with thionoesters in the presence of a rhodium(II) catalyst. The resulting 3-sulfonyl-4-thiazolines subsequently aromatize into the corresponding 2,5-disubstituted thiazoles by elimination of the sulfonyl group. (Chemical Equation Presented).
Programmed synthesis of arylthiazoles through sequential C-H couplings
Tani, Satoshi,Uehara, Takahiro N.,Yamaguchi, Junichiro,Itami, Kenichiro
, p. 123 - 135 (2014/01/06)
A programmed synthesis of privileged arylthiazoles via sequential C-H couplings catalyzed by palladium or nickel catalysts has been accomplished. This versatile protocol can supply all possible arylthiazole substitution patterns (2-aryl, 4-aryl, 5-aryl, 2
Pd nanoparticle-silica nanotubes (Pd@SNTs) as an efficient catalyst for Suzuki-Miyaura coupling and sp2 C-H arylation in water
Park, Ginam,Lee, Sanghee,Son, Sang Jun,Shin, Seunghoon
supporting information, p. 3468 - 3473 (2013/12/04)
Silica nanotubes (SNTs) functionalized with Pd-NPs on the inner surface performed as efficient nano-reactors for C-C coupling in water; the nano-confinement offers minimized leaching of Pd and yet efficient mass transfer for Suzuki-Miyaura coupling and C-H arylation of thiazoles in water with very high TON.
A guideline for the arylation of positions 4 and 5 of thiazole via Pd-catalyzed cross-coupling reactions
H?mmerle, Johanna,Schnürch, Michael,Iqbal, Naseer,Mihovilovic, Marko D.,Stanetty, Peter
experimental part, p. 8051 - 8059 (2010/10/21)
The arylation of thiazoles in 4- and 5-position was investigated in detail. Suzuki-Miyaura and Stille cross-coupling reactions were tested using thiazoles either as halide or organometal species. The obtained results were critically compared to develop he
A systematic study of Suzuki-Miyaura cross-coupling reactions on thiazoleboronic esters in the 4- and 5-position
Schnuerch, Michael,Haemmerle, Johanna,Mihovilovic, Marko D.,Stanetty, Peter
experimental part, p. 837 - 843 (2010/09/18)
A systematic study of the Suzuki-Miyaura cross-coupling reaction of thiazoleboronic esters under microwave conditions is presented. Boronic acid esters were prepared in the 4- and 5-position of the thiazole ring and subsequently cross-coupled with a number of different (hetero)aryl halides. Yields of the coupling process depended on the reactivity of the boronic acid at the particular position in the thiazole system, as hydrolysis and subsequent deboronation was found to be a major side reaction. Georg Thieme Verlag Stuttgart.
A comparative study on stille cross-coupling reactions of 2-phenylthiazoles and 2-phenyloxazoles
Haemmerle, Johanna,Spina, Markus,Schnuerch, Michael,Mihovilovic, Marko D.,Stanetty, Peter
experimental part, p. 3099 - 3107 (2009/04/06)
A systematic study of the cross-coupling capability of the 4- and 5-positions of 2-phenylthiazoles and -oxazoles under Stille conditions is presented. The azoles were both applied as stannanes and as the halide component. The obtained results were compared regarding the position of the halide and Bu3Sn group. In order to establish a general reactivity platform for those heterocyclic systems, a broad variety of aromatic and heteroaromatic halides were coupled and some significant differences concerning the coupling properties of the investigated systems were observed. Georg Thieme Verlag Stuttgart.
Comparing the reactivity of the 4- and 5-positions of 2-phenylthiazoles in stille cross-coupling reactions
H?mmerle, Johanna,Schnürch, Michael,Stanetty, Peter
, p. 2975 - 2978 (2008/03/12)
A systematic study of the cross-coupling capability of 4-and 5-substituted 2-phenylthiazoles under Stille conditions is presented. Two cross-coupling options were investigated: 1) combination of thiazolylstannanes with various aryl(hetaryl) halides and, 2) reaction of halothiazoles with PhSn(Bu) 3 as coupling partner. The results obtained from the cross-coupling reactions on the 4- and 5-positions of the thiazole system were compared regarding the influence of the position of the halide (Br, I) and the Bu 3Sn group on both coupling partners. A broad selection of aromatic and heteroaromatic halides was coupled in order to establish a general reactivity platform for this heterocyclic system. Georg Thieme Verlag Stuttgart.
Direct arylation of thiazoles on water
Turner, Gemma L.,Morris, James A.,Greaney, Michael F.
, p. 7996 - 8000 (2008/09/17)
Wetter is better: The direct arylation of thiazoles on water is quicker, cleaner, and higher-yielding than arylation in organic solvents. The reaction works under mild conditions for an array of aryl iodides, producing 2,5-diaryl thiazoles in excellent yields. Importantly, novel bi-heteroaryl compounds are produced without the requirement for stoichiometric organometallic coupling agents. (Figure Presented).
General facile synthesis of 2,5-diarylheteropentalenes
Vachal, Petr,Toth, Leslie M.
, p. 7157 - 7161 (2007/10/03)
Palladium-catalyzed cross-coupling reactions of various heteropentalene derivatives were systematically studied. A general three-step synthesis of 2,5-diarylheteropentalenes involving two Suzuki or Negishi couplings and a regiospecific bromination was developed. Nonsymmetrical 2,5-diaryl-furans, thiophenes, pyrroles, 1,3-thiazoles, 1,3-oxazoles, 1,3,4-thiadiazoles, and 1,3,4-oxadiazoles were prepared in 31-67% isolated yield (three steps).
