1443984-93-7Relevant articles and documents
Light-induced metal-free transformations of unactivated pyridotriazoles
Zhang, Ziyan,Yadagiri, Dongari,Gevorgyan, Vladimir
, p. 8399 - 8404 (2019/09/30)
A highly efficient and practical method for incorporation of the arylmethylpyridyl moiety into diverse molecules has been developed. This method features the transition metal-free light-induced room temperature transformation of pyridotriazoles into pyridyl carbenes, which are capable of smooth arylation, X-H insertion, and cyclopropanation reactions. The synthetic usefulness of the developed method was illustrated in a facile synthesis of biologically active molecules.
Rh(I)/NHC*-Catalyzed site- and enantioselective functionalization of c(sp3)?H bonds toward chiral triarylmethanes
Kim, Ju Hyun,Gre?ies, Steffen,Boultadakis-Arapinis, Melissa,Daniliuc, Constantin,Glorius, Frank
, p. 7652 - 7656 (2018/05/23)
The first Rh(I)-catalyzed asymmetric approach for the intermolecular functionalization of C(sp3)?H bonds is reported. For the first time, unsymmetrical N-heterocyclic carbenes (NHCs) were used for asymmetric catalysis that is capable of achieving not only high site-selectivity but also enantioselectivity. The Rh(I)/NHC* catalytic systems were applied to asymmetric direct C(sp3)?H arylation, which provides a synthetic route toward enantioenriched triarylmethanes.
Additive effects on palladium-catalyzed deprotonative-cross-coupling processes (DCCP) of sp3 C-H bonds in diarylmethanes
Bellomo, Ana,Zhang, Jiadi,Trongsiriwat, Nisalak,Walsh, Patrick J.
, p. 849 - 857 (2013/03/28)
Palladium-catalyzed cross-coupling reactions have become one of the most useful tools in modern organic chemistry. Current methods to achieve direct functionalization of sp3 C-H bonds of arenes and heteroarenes often employ substrates with appropriately placed directing groups to enable reactivity. Examples of intermolecular arylation methods of weakly acidic sp3 C-H bonds in the absence of directing groups, however, are still limited. We describe herein a study on the use of additives in Pd-catalyzed deprotonative-cross-coupling processes (DCCP) of sp3 C-H bonds of diarylmethanes with aryl bromides at room temperature. These studies resulted in development of four new efficient Pd-catalyzed DCCP using additives that enabled the generation of a range of sterically and electronically diverse aryl- and heteroaryl containing triarylmethanes in good to excellent yields. Additive identification and optimization of all reaction conditions (additive loading, solvent and temperature) were performed using high-throughput experimentation (HTE). The approach outlined herein is expected to be generalizable to other C-H functionalization reactions involving the deprotonation of weakly acidic C-H bonds. The Royal Society of Chemistry 2013.
