Water as the Reaction Medium for Intermolecular C-H Alkane Functionalization in Micellar Catalysis

作者：Alvarez Maria; Gava Riccardo; Rodriguez Manuel R; Rull Silvia G; Perez Pedro J^*

来源：ACS Catalysis, 2017, 7(5): 3707-3711.

DOI：10.1021/acscatal.6b03669

• Alkane functionalization
• C-H activation
• catalysis in water
• carbene transfer
• copper and silver catalysts

A series of alkanes CnH2n+2 have been functionalized in water as the reaction medium, using a silver-based catalyst, upon the insertion of carbene (CHCO2Et from N2CHCO2Et) groups into the carbon hydrogen bonds of hexane, cyclohexane, or 2-methylbutane, among others. The regioselectivity toward the distinct reaction sites is identical to that found in neat alkane, the water-based system allowing the use of a much shorter excess of the hydrocarbon. This is the first example of the intermolecular functionalization of alkanes with this strategy in water. The functionalized alkanes partially undergo the incorporation of a second carbene unit to provide alpha-(acyloxy)acetates, in an unprecedented tandem reaction of this nature.

• 出版日期2017-5