Palladium-Catalyzed Enantioselective Arylation of Aryl Sulfenate Anions: A Combined Experimental and Computational Study
作者： Tiezheng Jia , Mengnan Zhang , Samuel P. McCollom , Ana Bellomo , Sonia Montel
DOI: 10.1021/JACS.7B03623
关键词: Medicinal chemistry 、 Aryl 、 Chemistry 、 Moiety 、 Catalysis 、 Transmetalation 、 Organic chemistry 、 Enantioselective synthesis 、 Palladium 、 Oxidative addition 、 Bromide
摘要: A novel approach to produce chiral diaryl sulfoxides from aryl benzyl and bromides via an enantioselective arylation of sulfenate anions is reported. (JosiPhos)Pd-based catalyst successfully promotes the asymmetric reaction with good functional group compatibility. wide range enantioenriched diaryl, heteroaryl, even diheteroaryl were generated. Many prepared herein would be difficult prepare classic oxidation sulfides, including Ph(Ph-d5)SO (90% ee, 95% yield). DFT-based computational study suggested that induction originates two primary factors: (i) both a kinetic thermodynamic preference for oxidative addition places bromide trans JosiPhos-diarylphosphine moiety (ii) Curtin–Hammett-type control over interconversion between O- S-bound isomers palladium species following rapid re- si-bound transmetalation products, r...
acs.org
sci-hub.se 参考文章(75)
Mengnan Zhang, Tiezheng Jia, Carol Y. Wang, Patrick J. Walsh, Organocatalytic Synthesis of Alkynes Journal of the American Chemical Society. ,vol. 137, pp. 10346- 10350 ,(2015) , 10.1021/JACS.5B06137
Markus Jakt, Linus Johannissen, Henry S. Rzepa, David A. Widdowson, René Wilhelm, A computational study of the mechanism of palladium insertion into alkynyl and aryl carbon–fluorine bonds Journal of The Chemical Society-perkin Transactions 1. pp. 576- 581 ,(2002) , 10.1039/B108727B
Gellért Sipos, Emma E. Drinkel, Reto Dorta, The emergence of sulfoxides as efficient ligands in transition metal catalysis. Chemical Society Reviews. ,vol. 44, pp. 3834- 3860 ,(2015) , 10.1039/C4CS00524D
Rajendra D. Mahale, Mahesh R. Rajput, Golak C. Maikap, Mukund K. Gurjar, Davis Oxaziridine-Mediated Asymmetric Synthesis of Proton Pump Inhibitors Using DBU Salt of Prochiral Sulfide Organic Process Research & Development. ,vol. 14, pp. 1264- 1268 ,(2010) , 10.1021/OP100075V
David S. Surry, Stephen L. Buchwald, Diamine ligands in copper -catalyzed reactions Chemical Science. ,vol. 1, pp. 13- 31 ,(2010) , 10.1039/C0SC00107D
Elise Bernoud, Gaëtan Le Duc, Xavier Bantreil, Guillaume Prestat, David Madec, Giovanni Poli, Aryl sulfoxides from allyl sulfoxides via [2,3]-sigmatropic rearrangement and domino Pd-catalyzed generation/arylation of sulfenate anions. Organic Letters. ,vol. 12, pp. 320- 323 ,(2010) , 10.1021/OL902620T
Fulvio Di Furia, Giorgio Modena, Roberta Seraglia, Synthesis of Chiral Sulfoxides by Metal-Catalyzed Oxidation with t-Butyl Hydroperoxide Synthesis. ,vol. 1984, pp. 325- 326 ,(1984) , 10.1055/S-1984-30829
Mona El-Aasr, Yukio Fujiwara, Motohiro Takeya, Tsuyoshi Ikeda, Sachiko Tsukamoto, Masateru Ono, Daisuke Nakano, Masafumi Okawa, Junei Kinjo, Hitoshi Yoshimitsu, Toshihiro Nohara, Onionin A from Allium cepa Inhibits Macrophage Activation Journal of Natural Products. ,vol. 73, pp. 1306- 1308 ,(2010) , 10.1021/NP100105U
Bing Zheng, Tiezheng Jia, Patrick J. Walsh, A General and Practical Palladium‐Catalyzed Direct α‐Arylation of Amides with Aryl Halides Advanced Synthesis & Catalysis. ,vol. 356, pp. 165- 178 ,(2014) , 10.1002/ADSC.201300851
Yoshiki Chujo, Toshiyuki Oyama, Kensuke Naka, Polymer Homologue of DMSO: Synthesis of Poly(ethylene sulfoxide) by Selective Oxidation of Poly(ethylene sulfide) Macromolecules. ,vol. 32, pp. 5240- 5242 ,(1999) , 10.1021/MA981639E