1209455-71-9Relevant academic research and scientific papers
Chromium(III)-Catalyzed C(sp2)-H Alkynylation, Allylation, and Naphthalenation of Secondary Amides with Trimethylaluminum as Base
Chen, Mengqing,Doba, Takahiro,Ilies, Laurean,Nakamura, Eiichi,Razumkov, Hlib,Sato, Takenari,Shang, Rui
, p. 4883 - 4891 (2020)
Among base metals used for C-H activation reactions, chromium(III) is rather unexplored despite its natural abundance and low toxicity. We report herein chromium(III)-catalyzed C(sp2)-H functionalization of an ortho-position of aromatic and α,β-unsaturated secondary amides using readily available AlMe3 as a base and using bromoalkynes, allyl bromide, and 1,4-dihydro-1,4-epoxynaphthalene as electrophiles. This redox-neutral reaction taking place at 70-90 °C, requires as low as 1-2 mol % of CrCl3 or Cr(acac)3 as a catalyst without any added ligand, and tolerates functional groups such as aryl iodide, boronate, and thiophene groups. Stoichiometric and kinetics studies as well as kinetic isotope effects suggest that the catalytic cycle consists of a series of thermally stable but reactive intermediates bearing two molecules of the amide substrate on one chromium atom and also that one of these chromate(III) complexes takes part in the alkynylation, allylation, and naphthalenation reactions. The proposed mechanism accounts for the effective suppression of methyl group delivery from AlMe3 for ortho-C-H methylation.
Nematicidal activities of diamides with diphenylacetylene scaffold against Meloidogyne Incognita
Li, Jiling,Zhang, Zhicheng,Xu, Xiaoyong,Shao, Xusheng,Li, Zhong
, p. 1543 - 1549 (2015/10/20)
With the goal of searching for new potential nematicides with high activity and low toxicity, new molecules are needed as potential prototypes for the synthesis of new nematicidal compounds. A series of novel diamides based on diphenylacetylene scaffold were designed and synthesised. The conformation of the amide was restricted through the ten-membered H-bonded ring. Their structures were characterised by 1H NMR, 13C NMR, 19F NMR, and high-resolution mass spectrometry. The preliminary bioassays evaluated against Meloidogyne Incognita indicated that most of the title compounds were endowed with moderate-to-good activities at the concentration of 25mgL-1. In particular, compounds 9a, 9c, 9g, 9h, 9k, and 9l displayed >50% nematicidal activity at 5mgL-1. It is possible that the novel diamides with diphenylacetylene scaffold, which possess good nematicidal activities, provide distinct nematicidal chemotypes that can be used as leads for further optimisation.
Dichotomous control of E/Z-geometry in intramolecular cyclization of o-alkynylbenzamide derivatives catalyzed by organic superbase P4-tBu in the presence/absence of water
Kanazawa, Chikashi,Terada, Masahiro
supporting information; experimental part, p. 1668-1672+1637 (2010/07/03)
E/Z does it! An intramolecular cycli-zation reaction of o-alkynylbenzamides that allows dichotomous control of E/Z-geometry has been developed using an organic superbase, P4-tBu, as a catalyst. The presence/absence of water along with the use of an organi
