Iridium-catalyzed diborylation of benzylic C–H bonds

Arene C(sp2)-H bond borylation reactions provide rapid and efficient routes to synthetically versatile boronic esters. While iridium catalysts are well established for this reaction, the discovery and development of methods using Earth-abundant alternatives is limited to just a few examples. Applying an in situ catalyst activation method using air-stable and easily handed reagents, the iron Molecules | Free Full-Text | Weinreb Amides as Directing Weinreb amides are a privileged, multi-functional group with well-established utility in classical synthesis. Recently, several studies have demonstrated the use of Weinreb amides as interesting substrates in transition metal-catalyzed C-H functionalization reactions. Herein, we review this part of the literature, including the metal catalysts, transformations explored so far and specific Silanol: a traceless directing group for Pd-catalyzed o Jul 21, 2011 S. M. PRESHLOCK, D. L. PLATTNER, P. E. MALIGRES, S. W

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

Dec 02, 2013 Publications - Glorius Research Group

group can function as a traceless directing group for C!H borylation reactions of nitrogen heterocycles and anilines. We have previously demonstrated that the tert-butoxy-carbonyl (Boc) group can be used as a directing group in Ir-catalyzed borylations of nitrogen-containing heterocycles, such as pyrroles, indoles, azaindoles, and pyrazoles.[5b

Gevorgyan, V. “Silanol: A Traceless Directing Group for Pd-catalyzed o-Alkeneylation of Phenols”  J. Am. Chem. Soc. 2011, 133, 12406-12409 (Highlighted by Nature Chemistry 2014, 6, 94-96 [link] Publications | The Hartwig Group Hartwig Group - Publications. 69. Alcazar-Roman, L. M., Hartwig, J. F., Rheingold, A. L., Liable-Sands, L. M., and I. A. Guzei Mechanistic studies of the palladium-catalyzed amination of aryl halides and the oxidative addition of aryl bromides to Pd(BINAP)2 and Pd(DPPF)2: An unusual case of zero-order kinetic behavior and product inhibition. Catalyst-enabled Site-selectivity in the Iridium-catalyzed The same group subsequently found an intriguing switch of the site-selectivity from the para- to the meta-position in the C–H borylation of aromatic substrates bearing N,N-disubstituted amides using L3 (Figure 8 d). 36b For example, the C–H borylation of N,N-dimethylbenzamide proceeded with high meta-selectivity under conditions similar to Publications - Mitch Smith “Recent Advances and Challenges of Electrocatalytic N 2 Reduction to Ammonia,” Qing, G.; Ghazfar, R.; Jackowski, S. T.; Habibzadeh, F.; Ashtiani, M. M.; Chen, C