On November 2, 2018, Patel, Nitinchandra D.; Sieber, Joshua D.; Tcyrulnikov, Sergei; Simmons, Bryan J.; Rivalti, Daniel; Duvvuri, Krishnaja; Zhang, Yongda; Gao, Donghong A.; Fandrick, Keith R.; Haddad, Nizar; Lao, Kendricks So; Mangunuru, Hari P. R.; Biswas, Soumik; Qu, Bo; Grinberg, Nelu; Pennino, Scott; Lee, Heewon; Song, Jinhua J.; Gupton, B. Frank; Garg, Neil K.; Kozlowski, Marisa C.; Senanayake, Chris H. published an article.Formula: C6H10Cl3NO The title of the article was Computationally Assisted Mechanistic Investigation and Development of Pd-Catalyzed Asymmetric Suzuki-Miyaura and Negishi Cross-Coupling Reactions for Tetra-ortho-Substituted Biaryl Synthesis. And the article contained the following:
Metal-catalyzed cross-coupling reactions are extensively employed in both academia and industry for the synthesis of biaryl derivatives for applications to both medicine and material science. Application of these methods to prepare tetra-ortho-substituted biaryls leads to chiral atropisomeric products that introduce the opportunity to use catalyst control to develop asym. cross-coupling procedures to access these important compounds Asym. Pd-catalyzed Suzuki-Miyaura and Negishi cross-coupling reactions to form tetra-ortho-substituted biaryls were studied employing a collection of P-chiral dihydrobenzooxaphosphole (BOP) and dihydrobenzoazaphosphole (BAP) ligands. Enantioselectivities of up to 95:5 and 85:15 enantiomeric ratios were identified for the Suzuki-Miyaura and Negishi cross-coupling reactions, resp. Unique ligands for the Suzuki-Miyaura reaction vs the Negishi reaction were identified. A computational study on these Suzuki-Miyaura and Negishi cross-coupling reactions enabled an understanding in the differences between the enantiodiscriminating events between these two cross-coupling reactions. These results support that enantioselectivity in the Negishi reaction results from the reductive elimination step, whereas all steps in the Suzuki-Miyaura catalytic cycle contribute to the overall enantioselection with transmetalation and reductive elimination providing the most contribution to the observed selectivities. The experimental process involved the reaction of tert-Butyl trichloroacetimidate(cas: 98946-18-0).Formula: C6H10Cl3NO
The Article related to computationally assisted mechanistic investigation, palladium catalyst asym suzuki miyaura negishi cross coupling, tetra ortho substituted biaryl synthesis, palladium, asymmetric, catalysis, cross-coupling, phosphines and other aspects.Formula: C6H10Cl3NO
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