Transforming Matters

The team around Jinbo Hu (Shanghai Institute of Organic Chemistry), often together with the labs of Prof. G. K. Surya Prakash, and Prof. George Olah (1994 Nobel Price in Chemistry), have been publishing a lot in recent years around new methods to introduced fluorinated rests in organic molecules. Knowing the increasing occurence of fluorinated compounds in both medicinal chemistry and agrochemistry, it is highly valuable to keep an eye on their developments:

1. Reagents

• Yanchuan Zhao, Weizhou Huang, Lingui Zhu and Jinbo Hu, “Preparation of Tri- and Difluoromethylsilanes via an Unusual Magnesium Metal-Mediated Reductive Tri- and Difluoromethylation of Chlorosilanes Using Tri- and Difluoromethyl Sulfides, Sulfoxides, and Sulfones” : J. Org. Chem., 2003, 68 (11), , 4457–4463. (DOI: 10.1021/jo030110z)

• Chuanfa Ni, Laijun Zhang and Jinbo Hu, “Synthesis of Fluorinated β-Ketosulfones and gem-Disulfones by Nucleophilic Fluoroalkylation of Esters and Sulfinates with Di- and Monofluoromethyl Sulfones” : J. Org. Chem., 2009, 74 (10), , 3767–3771. (DOI: 10.1021/jo900320b)

2. Nucleophilic Addition of CF3-, CHF2- or CH2F- equivalents to C=O or C=N bonds: synthesis of alpha-fluoromethylated alcohols and amines

Read more…

• Chutian Shu, Kanwar Sidhu, Li Zhang, Xiao-jun Wang, Dhileepkumar Krishnamurthy, and Chris H. Senanayake, “Palladium-Catalyzed Cross-Coupling of Cyclopropylmagnesium Bromide with Aryl Bromides Mediated by Zinc Halide Additives”J. Org. Chem., 2010, 75 (19), , 6677–6680. (DOI: 10.1021/jo100983c)

• Lensey L. Hill, Jason L. Crowell, Strudwick L. Tutwiler, Nicholas L. Massie, C. Corey Hines, Scott T. Griffin, Robin D. Rogers, Kevin H. Shaughnessy, Gabriela A. Grasa, Carin C. C. Johansson Seechurn, Hongbo Li, Thomas J. Colacot, Joe Chou and Christopher J. Woltermann, J. Org. Chem., 2010, 75 (19), , 6477–6488. (DOI: 10.1021/jo101187q)

• Aaron D. Finke, Eric C. Elleby, Michael J. Boyd, Haim Weissman and Jeffrey S. Moore, “Zinc Chloride-Promoted Aryl Bromide−Alkyne Cross-Coupling Reactions at Room Temperature”J. Org. Chem., 2009, 74 (22), , 8897–8900. (DOI: 10.1021/jo902015w)

• Arash Soheili, Jennifer Albaneze-Walker, Jerry A. Murry, Peter G. Dormer, David L. Hughes, “Efficient and General Protocol for the Copper-Free Sonogashira Coupling of Aryl Bromides at Room Temperature”Org. Lett.2003, 5 (22), , 4191–4194. (DOI: 10.1021/ol035632f)

• Thomas Hundertmark, Adam F. Littke, Stephen L. Buchwald, and Gregory C. Fu, “Pd(PhCN)2Cl2/P(t-Bu)3: A Versatile Catalyst for Sonogashira Reactions of Aryl Bromides at Room Temperature”Org. Lett.2000, 2 (12), , 1729–1731. (DOI: 10.1021/ol0058947)

10.1021/ol1023085