Polyhedron p. 273 - 282 (2016)
Update date:2022-07-30
Topics: Synthesis Catalytic Activity Theoretical Study X-ray Characterization Sulfur ylide Suzuki-Miyaura reaction
Sabounchei
Yousefi
Ahmadianpoor
Hashemi
Bayat
Sedghi
Bagherjeri
Gable
The new sulfonium salt [SMe2CH2C(O)C6H4-m-OCH3]Br (1) was synthesized from the reaction of dimethyl sulfide and 2-bromo-3′-methoxyacetophenone. Further treatment with NaOH 10% gave the α-keto stabilized sulfur ylide SMe2C(H)C(O)C6H4-m-OCH3 (2). This ligand was reacted with the dichloro(1,5-cyclooctadiene)palladium(II) complex, [PdCl2(cod)], in a 2:1 ratio to give the new Cα-coordinated complexes cis- and trans-[PdCl2(SMe2C(H)C(O)C6H4-m-OCH3)2] (3a and 3b). Characterization of the obtained compounds was performed by elemental analysis, IR, 1H, 13C NMR and mass spectroscopies. Since complexes 3a and 3b were insoluble in most organic solvents, we chose DMSO as a suitable solvent for the NMR spectroscopies. Crystallization of above solution led to the formation of single crystals. The X-ray analysis results revealed that complex 3a has undergone a ligand replacement reaction and the complex [PdCl2(SMe2C(H)C(O)C6H4-m-OCH3)·DMSO] (4) was formed. This complex has two Cl atoms in cis positions, one sulfur ylide and one S-coordinated DMSO as ligands. The air/moisture stable complexes 3a and 3b were employed as efficient catalysts for the Suzuki-Miyaura cross-coupling reaction of several aryl halides. The coupled products of these reactions were obtained in good to excellent yields and purity, with short reaction times and low catalyst loading. Also a theoretical study on the structure and nature of the Pd-C bond in complex 4 is reported here at the BP86/def2-SVP level of theory.
View Morewebsite:http://www.afinechem.com
Contact:+86-571-85134551
Address:No. 206 Zhen Hua Road, Hangzhou 310030, Zhejiang, China
FUJIAN SHANSHUI CHEMICAL CORP.LTD.
Contact:+86-151-59920036
Address:Jinqiao Gareden, jo@fj-xinyi.com
Nanjing distinctions Medical Technology Co., Ltd.(expird)
Contact:+86-15996203785 13914714059
Address:nanjing,jiangsu , China
Chengdu Boon Stream Chemical Industry Co.,Ltd.
Contact:+86-28-83156758
Address:No.859,Dongzikou Road,Jinniu District,Chengdu,Sichuan,P.R.China
HUNAN CHEMAPI BIOLOGICAL TECHNOLOGY CO.,LTD.
Contact:+86-186-02659358
Address:1004, building 3, Wanke Jinsemaitianyuan, 498 Guitang Road, Yuhua District, Changsha City, Hunan Province, China
Doi:10.1039/c2cc30510k
(2012)Doi:10.1002/cjoc.201100256
(2012)Doi:10.1021/acs.joc.7b01206
(2017)Doi:10.1139/v2012-054
(2012)Doi:10.1002/jccs.202000517
(2021)Doi:10.1016/j.tetlet.2012.03.032
(2012)