1268451-48-4Relevant academic research and scientific papers
Corrigendum to: Ligand-Controlled Regiodivergent Pathways of Rhodium(III)-Catalyzed Dihydroisoquinolone Synthesis: Experimental and Computational Studies of Different Cyclopentadienyl Ligands (Chemistry - A European Journal, (2014), 20, 47, (15409-15418), 10.1002/chem.201404515)
Wodrich, Matthew D.,Ye, Baihua,Gonthier, Jér?me F.,Corminboeuf, Clémence,Cramer, Nicolai
supporting information, p. 7727 - 7727 (2020/06/16)
The authors became aware that product 4aa was erroneously assigned to 4-phenyl- 3,4-dihydroisoquinolin-1(2H)-one. Reanalysis of the 1H NMR and 13C NMR spectra of product 4aa confirmed that the correct structure corresponds to the constitutional 3-benzyl-isoindolones isomer (Figure 1). 4-Phenyl-3,4-dihydroisoquinolin-1(2H)-one was reported by Ellman and its structure was confirmed by X-ray crystallographic analysis.[1] The corrected isoindolone structure of 4aa matches all data of 3-benzylisoindolone synthesized by a different route.[2]. (Figure presented.).
Ligand-Controlled Regiodivergent Pathways of Rhodium(III)-Catalyzed Dihydroisoquinolone Synthesis: Experimental and Computational Studies of Different Cyclopentadienyl Ligands
Wodrich, Matthew D.,Ye, Baihua,Gonthier, Jér?me F.,Corminboeuf, Clémence,Cramer, Nicolai
supporting information, p. 15409 - 15418 (2016/02/18)
RhIII-catalyzed directed C-H functionalizations of arylhydroxamates have become a valuable synthetic tool. To date, the regioselectivity of the insertion of the unsaturated acceptor into the common cyclometalated intermediate was dependent solely on intrinsic substrate control. Herein, we report two different catalytic systems that allow the selective formation of regioisomeric 3-aryl dihydroisoquinolones and previously inaccessible 4-aryl dihydroisoquinolones under full catalyst control. The differences in the catalysts are computationally examined using density functional theory and transition state theory of different possible pathways to elucidate key contributing factors leading to the regioisomeric products. The stabilities of the initially formed rhodium complex styrene adducts, as well as activation barrier differences for the migratory insertion, were identified as key contributing factors for the regiodivergent pathways. RhIII-catalyzed directed C-H functionalization of aryl hydroxamates enables the selective formation of regioisomeric 3-aryl or 4-aryl dihydroisoquinolones with two different catalytic systems. The different selectivities are examined using DFT and transition state theory. The stabilities of the rhodium complex adducts and migratory-insertion activation barriers are key factors for the regiodivergent pathways (see scheme; rs=regioselectivity).
Ruthenium-catalyzed oxidative C - H bond olefination of N -methoxybenzamides using an oxidizing directing group
Li, Bin,Ma, Jianfeng,Wang, Nuancheng,Feng, Huiliang,Xu, Shansheng,Wang, Baiquan
supporting information; experimental part, p. 736 - 739 (2012/04/17)
Ruthenium-catalyzed oxidative C - H bond olefination of N-methoxybenzamides using an oxidizing directing group with a broad substrate scope is reported. The reactions of N-methoxybenzamides with acrylates in MeOH and styrene (or norbornadiene) in CF3
Rh(III)-catalyzed Directed C-H Olefination using an oxidizing directing group: Mild, efficient, and versatile
Rakshit, Souvik,Grohmann, Christoph,Besset, Tatiana,Glorius, Frank
, p. 2350 - 2353 (2011/05/04)
An efficient Rh(III)-catalyzed oxidative olefination by directed C-H bond activation of N-methoxybenzamides is reported. In this mild, practical, selective, and high-yielding process, the N-O bond acts as an internal oxidant. In addition, simply changing the substituent of the directing/oxidizing group results in the selective formation of valuable tetrahydroisoquinolinone products.
