A traceless directing group for C-H borylation. Angew Chem Int Ed Engl . 2013; 52(49): 12915-12919. doi: 10.1002/anie.201306511 Kuninobu Y, Ohmura T, Iwanaga T, Takai K. Palladium-catalyzed ortho selective C-H borylation of 2-phenylpyridine and its derivatives at room temperature .
Modifiable/Traceless Si-Tethered Directing Group for C–H Acyloxylation of Arenes.” 27th Herbert C. Brown Lectures, Purdue University, West Lafayette, IN, April 24, 2010 (poster, Best Poster Award). Nov 12, 2013 · A Traceless Directing Group for C H Borylation † Sean M. Preshlock Department of Chemistry, Michigan State University, 578 S Shaw Lane, East Lansing, MI 48824‐1322 (USA) A highly efficient and general protocol for traceless, directed C3-selective C-H borylation of indoles with [Ni(IMes)2] as the catalyst is reported. Activation and borylation of N-H bonds by [Ni(IMes)2] is essential to install a Bpin moiety at the N-position as a traceless directing group, which enables the C3-selective borylation of C-H bonds. The N-Bpin group which is formed is easily The protocol developed by Smith and Maleczka can be used as an example here, with the Bpin group serving as a traceless directing group for the selective C−H borylation of indoles into the 3
C−H bond which renders the reaction to directly occur on the aryl ring rather than at the vinylic carbon site newly palladated by the palladium migration.4b Recently, Lin, Feng, and Zhang et al. realized the C−H borylation,9a alkenylation,9b and arylation/annulation9c of gem-diaryl alkenes through aryl to vinyl 1,4-palladium migration
D maiti group iit bombay publications. 45. Direct Arylation via C-H Activation (Book Chapter) New Trends in Cross Coupling: Theory and Application.
functionalization of meta C—H’s is hard to achieve due to deactivation by the necessary electron-withdrawing directing groups. The dependence on directing group’s electronic effects further limits the application of the conventional methods. Functionalization of meta-C—H bonds therefore remains a
Jan 01, 2017 · In 2011, Larrosa and co-workers disclosed a method for formal meta-C H arylation using carboxylic acids as a traceless ortho-directing group (Scheme 8.43) with aryl iodides as coupling partners, which was compatible with a wide range of meta-substituents (Scheme 8.44). 84 Importantly, this tandem directed C H arylation/protodecarboxylation Undirected C-H Bond Activation of Arenes: [Rh(III)Cp*]-Catalyzed Dehydrogenative Alkene-Arene Coupling as New Pathway for the Selective Synthesis of Highly Substituted Z-Olefins, Chem. Asian J. 2012 , 7 , 1208-1212. Jul 21, 2011 · Transition metal-catalyzed directed C–H 7 alkenylaton 8 reactions have emerged as attractive alternative to the Mizoroki-Heck reaction. A directing group is usually introduced to control the regioselectivity as well as to enhance the reactivity of the reaction. 9 We were intrigued by the possibility to develop a method that would employ an easily removable directing group at the phenol The ligand-enabled development of ortho and meta C-H borylation of aromatic aldehydes is reported. It was envisaged that while ortho borylation could be achieved using tert-butylamine as the traceless protecting/directing group, meta borylation proceeds via an electrostatic interaction and a secondary interaction between the ligand of the catalyst and the substrate.
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