You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content.2.1.2.1.1.5 Arylboronic Acids/Esters (Chan–Lam–Evans Coupling)
Please login or sign up for a free trial to access the full content.
Hay, M. B.; Hicks, J. D., Science of Synthesis: Cross Coupling and Heck-Type Reactions, (2013) 2, 129.
Chan, Lam, and Evans pioneered the field of copper-mediated couplings of arylboronic acids with nitrogen nucleophiles.[28,29] Although the original methods for oxidative C—N coupling utilize stoichiometric copper, more recent developments have rendered the reaction catalytic through the use of oxygen as a terminal oxidant.[30,31] Couplings of primary aromatic amines with arylboronic acids are typically performed with a copper(II) salt such as copper(II) acetate in toluene or a halogenated solvent in the presence or absence of base. Molecular sieves are often added to remove water, preventing undesired phenol formation. Coupling typically occurs at room temperature, providing an advantage over standard cross-coupling methods for sensitive substrates.
Mee eeeeeeee ee e eeee-eeeee eeeeeeeeee eeee, eeee ee eeeeeeeeeeeee eeee (eeeeeeee eeee) ee eeeeeeee eeee, ee eeeeeeeee eeeeeeeee eeee eeeeee(MM) eeeeeee eee eeee eeeee ee eeeeeee eee eeeeeeee eeee.[88] Meeee eeeeeeeee eee eeeeeeee ee eeeeeeeeee ee eee eeeeee eee eeeeeee eeeeeeee eeeeeeeeee. M eeeeeee ee eeeeeeee-eeee, eeeeeeee-eeeeeeeee, eee eeeeeeeeee eeeeeeeee eeeeeeee eeee eeee eeeeeeeeeeee eeeeeee eeee 8-eeeeeeeeeeee eeee ee eeee eeeeeeee 88 (Me8 = 8-Mee) eeeee eee eeeeeeee eeeeee eeeee ee eeeeee(MM) eeeeeee/eeeeeeeeeeeee eeee (Meeeee 88). Meeeeeee eeee eeeeee ee eeeeeeee ee e eeeeeee ee eeeeeee eeeeeeee eeeeeeee, ee eeeeeee ee ee eeeeeeee eeee eeeeeeeee ee eee eeeeeeeeeee eee eeeeee eeeeeeeeeee ee eee eeeeeee eeee. Meeeeeee ee eeeeeee eeee eeeeeeee-eeeeeeeee 8-eeeeeeeeeeeee eeee eeeeeeee 88% eeeee eeeeeee eeeeeeeeee eeeeeeeeee 8-eeeeeeeeeeee eeee eeeeeeee eeee 88% eeeee. Meee eeeeee-eeeeeeeee eeeeee eee eeee eeee eeeeeeee ee Meeeeee ee eee eeeeeeeeeeeeeeeee ee eeeeeeeeeee eeeee eeeeeeeee ee eeeeeee-eeeeeeeee eeeeeeeeee.[88]
Meeeee 88 Meeeeeeee Meeeeeee ee Meeeeeeeeee Meeee eeee Meeeeee Meeeeeee Meeeee[88,88]
Meeeeeee eeeeeeeeee eeee eeee eeeeeeeee eee eee M-eeeeeeeee eeeee eeeeeeeeeeeeeeeeeeeeeeee eeee eee ee eee eeee eeeeeeeeeee ee eeee eeeeeeee (Meeeee 88).[88] Meeeee(MM) eeeeeee ee eeeee eeeeeee ee eee eeeeeee ee eeee eeeeeeee eeee eeeeee eee e eeeeeee ee eeeeeee eeeeeeee eeeeeeee.
Meeeee 88 M-Meeeeeeee Meeee Meeeeeeeeeeeeeeeeeeeeeee Meee[88]
Meeeeee eeeeeee eeee eeeeeeeeeee eeee eeee eeeeeeee ee eee eeeeee-eeeeeeeee eeeeeeee eeee eeeeeee eeeeeeee eeeeee (Meeeee 88). Meeeeeeeeee eeeee eee eeee eeeeeeeeeeee eeee eeee eeee eeeee ee ee eeeeeeeeee eeeeeeee eeeeeeee, eeeeeee eeeeeeeee eeeeeeeeeeeeeee eeeee eeee eee eee eeeeee ee ee eeeeeeee eeeeeeee eeeeeeee.[88,88] Meeeeeeeeeee, Meeeeee eee ee-eeeeeee eeee eeeee eeee eeeeeee eeeeeeeee eeeeeeeee ee eee eeeeeee eeee ee eeee eeeeeeee.[88]
Meeeee 88 Meeeeeeeee ee Meeee-Meeeeeeeee Meeeeeee Meeeeeee[88,88]
Meeeeeeeeeee Meeeeeeee
Meeeeeeeeeee 88; Meeeeee Meeeeeeee:[88]
Mee eeeeeeeeeee eeee (8.8 eeeee), Me(MMe)8 (8–88 eee%), eee eeeeeeeeeeeee eeee (88–88 eee%) eeee eeeeeeee ee e 888-eM eeeee-eeeeeeee eeeee eeee e eeeee eeeeeeee eeeeeee eee. M eeeeee eeeeee eee eeeeeeee, eee eee eeeeeee (8.8 M), 8,8-eee (8.8 eeeee), eee eee eeeeeeeee (8.8 eeeee) eeee eeeeeeeeeeee eeeee ee eeeeeee. Mee eeeeeeeee eeeeeee eee eeeeeee ee e eeee eeee eee 88 e, eeeeeee eeee MeMMe, eeeeeeee eeeeeee e eeee ee eeeeee eee, eee eeee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee).
References
eng_Latn eng_Latn eng_Latn eng_Latn eng_Latn bam_Latn bam_Latn bam_Latn bam_Latn bam_Latn bam_Latn bam_Latn bam_Latn bam_Latn lvs_Latn