Ruthenium-catalyzed synthesis of: N -substituted lactams by acceptorless dehydrogenative coupling of diols with primary amines
Herein, we report the first example of synthesis of N-substituted lactams via an acceptorless dehydrogenative coupling of diols with primary amines in one step, which was enabled by combining Ru3(CO)12 with a hybrid N-heterocyclic carbene-phosphine-phosphine ligand as the catalyst.
Ruthenium-Pincer-Catalyzed Hydrogenation of Lactams to Amino Alcohols
By using the commercially available ruthenium pincer complex (Ru-MACHO-BH) as a catalyst, the challenging direct hydrogenation of lactams and analogues has been successfully accomplished to deliver corresponding value-added amino alcohols in good-to-excellent yields under mild reaction conditions. Remarkably, in addition to N-protected lactams, unprotected ones could also be readily reduced in the presence of a catalytic amount of weak base or even under neutral reaction conditions, which further highlights the broad substrate scope and the protocol efficiency.
Chen, Jiangbo,Wang, Jiaquan,Tu, Tao
p. 2559 - 2565
(2018/07/30)
Transition-Metal-Free Amine Oxidation: A Chemoselective Strategy for the Late-Stage Formation of Lactams
A metal-free strategy for the formation of lactams via selective oxidation of cyclic secondary and tertiary amines is described. Molecular iodine facilitates both chemoselective and regioselective oxidation of C-H bonds directly adjacent to a cyclic amine. The mild conditions, functional group tolerance, and substrate scope are demonstrated using a suite of diverse small molecule cyclic amines, including clinically approved drug scaffolds.
Griffiths, Robert J.,Burley, Glenn A.,Talbot, Eric P. A.
p. 870 - 873
(2017/02/26)
Reaction of β-, γ-, and δ-chloroalkanamides with potassium tert-butoxide in tetrahydrofuran: Elimination, and lactamization
γ- and δ-Chloroalkanamides were found to undergo lactamization readily when treated with potassium tert-butoxide in tetrahydrofuran. Raising the reaction temperature may encourage SN2 displacement reaction. On the other hand β-chloroalkanamides only undergo elimination, followed by dimerization and trimerization of the acrylamide initially formed.
Wang, Eng Chi,Lin, Huey-Jen
p. 481 - 489
(2007/10/03)
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