313516-35-7Relevant articles and documents
Copper-Catalyzed C(sp3)?H Amidation: Sterically Driven Primary and Secondary C?H Site-Selectivity
Bakhoda, Abolghasem (Gus),Jiang, Quan,Badiei, Yosra M.,Bertke, Jeffery A.,Cundari, Thomas R.,Warren, Timothy H.
supporting information, p. 3421 - 3425 (2019/02/14)
Undirected C(sp3)?H functionalization reactions often follow site-selectivity patterns that mirror the corresponding C?H bond dissociation energies (BDEs). This often results in the functionalization of weaker tertiary C?H bonds in the presence of stronger secondary and primary bonds. An important, contemporary challenge is the development of catalyst systems capable of selectively functionalizing stronger primary and secondary C?H bonds over tertiary and benzylic C?H sites. Herein, we report a Cu catalyst that exhibits a high degree of primary and secondary over tertiary C?H bond selectivity in the amidation of linear and cyclic hydrocarbons with aroyl azides ArC(O)N3. Mechanistic and DFT studies indicate that C?H amidation involves H-atom abstraction from R-H substrates by nitrene intermediates [Cu](κ2-N,O-NC(O)Ar) to provide carbon-based radicals R. and copper(II)amide intermediates [CuII]-NHC(O)Ar that subsequently capture radicals R. to form products R-NHC(O)Ar. These studies reveal important catalyst features required to achieve primary and secondary C?H amidation selectivity in the absence of directing groups.
CuH-Catalyzed Asymmetric Hydroamidation of Vinylarenes
Zhou, Yujing,Engl, Oliver D.,Bandar, Jeffrey S.,Chant, Emma D.,Buchwald, Stephen L.
supporting information, p. 6672 - 6675 (2018/06/11)
A CuH-catalyzed enantioselective hydroamidation reaction of vinylarenes has been developed using readily accessible 1,4,2-dioxazol-5-ones as electrophilic amidating reagents. This method provides a straightforward and efficient approach to synthesize chiral amides in good yields with high levels of enantiopurity under mild conditions. Moreover, this transformation tolerates substrates bearing a broad range of functional groups.
An efficient and convenient synthesis of N-substituted amides under heterogeneous condition using Al(HSO4)3 via Ritter reaction
Karimian, Elnaz,Akhlaghinia, Batool,Ghodsinia, Sara S.E.
, p. 429 - 439 (2016/03/16)
An efficient and inexpensive synthesis of N-substituted amides from the reaction of aliphatic and aromatic nitriles with various benzylic alcohols (secondary and tertiary) and tert-butyl alcohol by refluxing nitromethane via the Ritter reaction catalyzed by aluminum hydrogen sulfate [Al(HSO4)3] is described. The catalyst which is an air-stable, cost-effective solid acid could be readily recycled by filtration and reused four times without any significant loss of its activity. [Figure not available: see fulltext.]
2-Trifluoroacetylthiophenes, a novel series of potent and selective class II histone deacetylase inhibitors
Jones, Philip,Bottomley, Matthew J.,Carfi, Andrea,Cecchetti, Ottavia,Ferrigno, Federica,Lo Surdo, Paola,Ontoria, Jesus M.,Rowley, Michael,Scarpelli, Rita,Schultz-Fademrecht, Carsten,Steinkuehler, Christian
scheme or table, p. 3456 - 3461 (2009/04/05)
The identification of class II HDAC inhibitors has been hampered by lack of efficient enzyme assays, in the preceding paper two assays have been developed to improve the efficiency of these enzymes: mutating an active site histidine to tyrosine, or by the
Palladium-catalyzed aminocarbonylation of aryl chlorides at atmospheric pressure: The dual role of sodium phenoxide
Martinelli, Joseph R.,Clark, Thomas P.,Watson, Donald A.,Munday, Rachel H.,Buchwald, Stephen L.
, p. 8460 - 8463 (2008/09/18)
(Chemical Equation Presented) No pressure, no worries: A general, functional-group-tolerant, mild system for the Pd-catalyzed carbonylation of aryl chlorides to the corresponding amides has been developed. The catalyst operates at 1 atm CO using an inexpensive, air-stable, and commercially available ligand (see scheme, Cy = cyclohexyl). Sodium phenoxide is a critical additive in this transformation; its role has been studied using in situ IR spectroscopy.
