Cu-Mediated trifluoromethylation of benzyl, allyl and propargyl methanesulfonates with TMSCF₃

• Xueliang Jiang and
• Feng-Ling Qing

Beilstein J. Org. Chem. 2013, 9, 2862–2865, doi:10.3762/bjoc.9.322

• 201620, China 10.3762/bjoc.9.322 Abstract A Cu-mediated trifluoromethylation of benzyl, allyl and propargyl methanesulfonates with TMSCF3 was developed for the first time. This method offers a convenient and economical approach to various trifluoroethyl-containing compounds. Keywords: copper

• ; methanesulfonates; organo-fluorine; trifluoromethylation; Introduction Fluorinated organic molecules are extremely important in agrochemicals, pharmaceuticals and materials [1][2][3][4][5][6]. In recent years, (trifluoroethyl)arenes have drawn increasing attention in medicinal chemistry and related fields [7][8][9

• here the first example of Cu-mediated trifluoromethylation of benzyl methanesulfonates (Scheme 1c). Results and Discussion We initiated our investigation by reacting benzyl methanesulfonate 1a with TMSCF3 (2.0 equiv) in the presence of KF (2.0 equiv) and CuI (0.2 equiv) in DMF (2.0 mL) at 60 °C under

Approaches to α-amino acids via rearrangement to electron-deficient nitrogen: Beckmann and Hofmann rearrangements of appropriate carboxyl-protected substrates

• Sosale Chandrasekhar and
• V. Mohana Rao

Beilstein J. Org. Chem. 2012, 8, 1393–1399, doi:10.3762/bjoc.8.161

• . Oximation of 2 to 3. Alkylketones 2 were converted to the corresponding oximes 3 with NH2OH·HCl-pyridine by standard procedures [26] and purified by crystallization (solids). Oxime methanesulfonates 4. Oximes 3 (1.0 mmol) in CH2Cl2 (3.0 mL) were cooled to −10 °C and treated with Et3N (1.2 mmol) followed by

Novel base catalysed rearrangement of sultone oximes to 1,2-benzisoxazole- 3-methane sulfonate derivatives

• Veera Reddy Arava,
• Udaya Bhaskara Rao Siripalli,
• Vaishali Nadkarni and
• Rajendiran Chinnapillai

Beilstein J. Org. Chem. 2007, 3, No. 20, doi:10.1186/1860-5397-3-20

• -3-methanesulfonates and 4-oximino-2,3-dihydrobenzoxathiin-2,2-dioxides (sultone oximes) is described. These compounds are important intermediates for the preparation of zonisamide, an anti-convulsant drug. Background 3-Alkyl-1,2-benzisoxazole derivatives are known to have important biological

• economical process for the preparation of 1,2-benzisoxazole-3-methanesulfonates from sultone oximes, which can be employed for the production of zonisamide and its derivatives. The 1,2-benzisoxazole-3-methanesulfonic acid sodium salt preparation has been filed as a PCT application. [5][6] Experimental See