Unknown

Dataset Information

0

Iridium-Catalyzed Silylation of Five-Membered Heteroarenes: High Sterically Derived Selectivity from a Pyridyl-Imidazoline Ligand.


ABSTRACT: The steric effects of substituents on five-membered rings are less pronounced than those on six-membered rings because of the difference in bond angles. Thus, the regioselectivities of reactions that occur with selectivities dictated by steric effects, such as the borylation of C-H bonds, have been poor in many cases. We report that the silylation of five-membered ring heteroarenes occurs with high sterically derived regioselectivity when catalyzed by the combination of [Ir(cod)(OMe)]2 and a phenanthroline ligand or a new pyridyl-imidazoline ligand that further increases the regioselectivity. The silylation reactions with these catalysts produce high yields of heteroarylsilanes from functionalization at the most sterically accessible C-H bonds of these rings under conditions that the borylation of C-H bonds with previously reported catalysts formed mixtures of products or products that are unstable. The heteroarylsilane products undergo cross-coupling reactions and substitution reactions with ipso selectivity to generate heteroarenes that bear halogen, aryl and perfluoroalkyl substituents.

SUBMITTER: Karmel C 

PROVIDER: S-EPMC7566956 | biostudies-literature |

REPOSITORIES: biostudies-literature

Similar Datasets

| S-EPMC6839914 | biostudies-literature
| S-EPMC5822728 | biostudies-literature
| S-EPMC7660231 | biostudies-literature
| S-EPMC3135680 | biostudies-literature
| S-EPMC8153796 | biostudies-literature
| S-EPMC5293510 | biostudies-literature
| S-EPMC3983327 | biostudies-literature
| S-EPMC7822902 | biostudies-literature
| S-EPMC6457191 | biostudies-literature
| S-EPMC7484944 | biostudies-literature