26167-26-0Relevant academic research and scientific papers
Synthesis of Tetraarylmethanes by the Triflic Acid-Promoted Formal Cross-Dehydrogenative Coupling of Triarylmethanes with Arenes
Nambo, Masakazu,Yim, Jacky C.-H.,Fowler, Kevin G.,Crudden, Cathleen M.
supporting information, p. 2936 - 2940 (2017/10/09)
The formal cross-dehydrogenative coupling of triarylmethanes with arenes promoted by triflic acid and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone is described. This method provides a variety of tetraarylmethane derivatives in good to excellent yields from triarylmethanes that can be readily prepared by our previous methods. Control experiments suggest a possible catalytic cycle involving the generation of a trityl cation intermediate followed by nucleophilic addition of the arene.
Synthesis of Di- and Triarylmethanes through Palladium-Catalyzed Reductive Coupling of N -Tosylhydrazones and Aryl Bromides
Xia, Yamu,Hu, Fangdong,Xia, Ying,Liu, Zhenxing,Ye, Fei,Zhang, Yan,Wang, Jianbo
, p. 1073 - 1086 (2017/02/24)
A palladium-catalyzed reductive coupling between N-tosylhydrazones and aryl bromides has been developed. The reaction provides an efficient method for the synthesis of diarylmethanes and triarylmethanes via the formation of C(sp2)-C(sp3) single bonds. This new methodology for the synthesis of diarylmethanes and triarylmethanes is featured by the ready availability of the starting materials, mild reaction conditions, and the tolerance of wide range of functional groups. The reaction follows a pathway including palladium carbene formation, migratory insertion, and reduction of the alkylpalladium(II) intermediate.
NiXantphos: A deprotonatable ligand for room-temperature palladium-catalyzed cross-couplings of aryl chlorides
Zhang, Jiadi,Bellomo, Ana,Trongsiriwat, Nisalak,Jia, Tiezheng,Carroll, Patrick J.,Dreher, Spencer D.,Tudge, Matthew T.,Yin, Haolin,Robinson, Jerome R.,Schelter, Eric J.,Walsh, Patrick J.
supporting information, p. 6276 - 6287 (2014/05/20)
Although the past 15 years have witnessed the development of sterically bulky and electron-rich alkylphosphine ligands for palladium-catalyzed cross-couplings with aryl chlorides, examples of palladium catalysts based on either triarylphosphine or bidentate phosphine ligands for efficient room temperature cross-coupling reactions with unactivated aryl chlorides are rare. Herein we report a palladium catalyst based on NiXantphos, a deprotonatable chelating aryldiphosphine ligand, to oxidatively add unactivated aryl chlorides at room temperature. Surprisingly, comparison of an extensive array of ligands revealed that under the basic reaction conditions the resultant heterobimetallic Pd-NiXantphos catalyst system outperformed all the other mono- and bidentate ligands in a deprotonative cross-coupling process (DCCP) with aryl chlorides. The DCCP with aryl chlorides affords a variety of triarylmethane products, a class of compounds with various applications and interesting biological activity. Additionally, the DCCP exhibits remarkable chemoselectivity in the presence of aryl chloride substrates bearing heteroaryl groups and sensitive functional groups that are known to undergo 1,2-addition, aldol reaction, and O-, N-, enolate-α-, and C(sp2)-H arylations. The advantages and importance of the Pd-NiXantphos catalyst system outlined herein make it a valuable contribution for applications in Pd-catalyzed arylation reactions with aryl chlorides.
Palladium-catalyzed diarylmethyl C(sp3)-C(sp2) bond formation: A new coupling approach toward triarylmethanes
Xia, Ying,Hu, Fangdong,Liu, Zhenxing,Qu, Peiyuan,Ge, Rui,Ma, Chen,Zhang, Yan,Wang, Jianbo
, p. 1784 - 1787 (2013/06/26)
Palladium-catalyzed reductive coupling reactions between N-tosylhydrazones and aryl halides lead to the formation of C(sp3)-C(sp2) bonds. This approach provides a general route for the synthesis of triarylmethanes.
