137669-14-8Relevant academic research and scientific papers
Iron-catalyzed coupling of aryl sulfamates and aryl/vinyl tosylates with aryl grignards
Agrawal, Toolika,Cook, Silas P.
supporting information, p. 5080 - 5083 (2014/12/11)
The iron-catalyzed coupling of aryl sulfamates and tosylates with aryl Grignard reagents is reported for the first time. The methodology employs air-stable, low-cost FeF3·3H2O and the N-heterocyclic carbene ligand IPr·HCl as the preligand to form a long-lived catalyst upon treatment with aryl Grignards. The reaction provides a range of cross-coupled products in good-to-excellent yields. In contrast to previous reports with aryl chlorides, these reactions proceed with low levels of Grignard homocoupling regardless of the iron source.
The Regioselective Cleavage of Aryl Tosylates by Electrochemical Reduction
Civitello, Edgar R.,Rapoport, Henry
, p. 834 - 840 (2007/10/02)
The electrochemical reductions of eight bis(tosyloxy)benzenoid compounds were studied as a method for the regioselective cleavage of aryl tosylates.For the methyl bis(tosyloxy)benzoate isomers, a strong preference was observed for cleavage of the tosyl group in conjugation with the electron-withdrawing ester moiety.Thus it was possible to selectively cleave tosyl groups to the ortho or para positions over tosyl groups at the meta positions.The bis(tosyloxy)anisole isomers displayed the opposite regioselectivity favoring cleavage of tosyl groups that were meta to the electron-donating methoxy substituent.The general electrochemical process for the reduction of aryl tosylates has been shown to be selective, high yielding, and reproducible on gram quantities.
