Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via
2.1.2.1.1.4.3 Aryl Methanesulfonates

DOI: 10.1055/sos-SD-208-00078

Hay, M. B.; Hicks, J. D.Science of Synthesis: Cross Coupling and Heck-Type Reactions, (20132128.

Aryl methanesulfonates are the least reactive electrophiles for the amination of aromatic amines, although they possess several advantageous properties, including higher stability relative to other sulfonates and increased atom economy in cross-coupling reactions.[‌17‌,‌73‌] Aryl methanesulfonate aminations typically involve palladium catalysts derived from electron-rich phosphines such as BrettPhos (2) or related ligands and are carried out in the presence of weak bases in alcoholic solvents at elevated temperature (Scheme 22).[‌17‌,‌73‌] Under these conditions, the reaction is successful, providing products 37 for a variety of electronically diverse aryl methanesulfonates and amines and tolerates a variety of functional groups, including enolizable ketones.[‌17‌,‌73‌]

Meeeee 88 Meeeeeeee-Meeeeeeee Meeeeeeee ee Meeeeee Meeeeeee Meeeee eeee Meee Meeeeeeeeeeeeeeee[‌88‌]

Meeeeeeeeee 88

Me8 Me8 Meeeeeee Meeeeeeeee Meeee (%) Mee
Me 8-e-MeM8M8 Me(MMe)8 (8 eee%), 8e M8MM8, e-MeMM, 888 °M 88 [‌88‌]
8,8-Me8M8M8 8,8-Me8M8M8 Me(MMe)8 (8 eee%), 88e M8MM8, e-MeMM, 888 °M 88 [‌88‌]

e Meeee (Me/eeeeee) 8:8.

e Meeee (Me/eeeeee) 8:8.

Meeeeeeeeeee Meeeeeeee

Meeeeeeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

Me eeee-eeeee eeee eeee eeeeeeee eeee e eeeeeeee eeeeeee eee eee e Meeeee eeeeee eee eeeeeee eeee Me(MMe)8 (8 eee%) eee MeeeeMeee (8; 8 eee%). Mee eeeeee eee eeeeeeeee eee eeeeeeeeee eeee eeeee (8 ×), eeeeeeee ee eeeeeeee ee e-MeMM (8 eM/eeee eeeeeeeee) eee eeeeeeee M8M (8 eee%). Mee eeee eee eeeeee ee 888 °M eee 8 eee. M eeeeee eeee-eeeee eeee eeee, eeeee eee eeeeeeee eeee e eeeeeeee eeeeeee eee eee eeeeee eeee e Meeeee eeeeee, eee eeeeeee eeee eee eeeeeeeeeeeeeeee (8 eeeee) eee M8MM8 (8.8 eeeee). Mee eeeeee eee eeeeeeeee eee eeeeeeeeee eeee eeeee (8 ×), eeeeeeee ee eee eeeeeeee ee eee eeeeeee (8.8 eeeee) eee e-MeMM (88 eM/eeee eeeeeeeee) eee eeeeeee. Mee eeeeeeeee eeeeeeee eeee eee eeeeeeeeeee eeee eee eeeee eeeeeeee eeeeee eeee eee eeeeee eee eeeeeee. Mee eeee eee eeeeee ee 888 °M eee 8 e, eeeeee ee ee, eeeeeee eeee MeMMe, eee eeeeee eeee M8M. Mee eeeeeee eeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee).

References


Cookie-Einstellungen