C-H activation and functionalization of pyridinoid azines {is a|is really a|is actually a|can be a|is often a|is usually a} {key|important|crucial|essential} transformation forthe synthesis of {many|numerous|several|a lot of|quite a few|lots of} {natural|all-natural|organic} {products|goods|items|merchandise|solutions}, pharmaceuticals, and {materials|supplies|components}. Reflecting the azinyl nitrogen lone-pair steric repulsion, tendency to irreversibly bind to metal ion catalysts, {and the|and also the|as well as the|along with the|plus the} electron-deficient nature of pyridine, C-H functionalization {at the|in the} {important|essential|crucial|critical|significant|vital} a-position remains {challenging|difficult}. {Thus|Therefore|Hence|As a result}, the {development|improvement} of earth abundant catalysts for the a-selective mono-functionalization of azines {is a|is really a|is actually a|can be a|is often a|is usually a} {crucial|essential|vital|critical|important} hurdle for {modern|contemporary|modern day} chemical synthesis. {Here|Right here}, the selective organolanthanide catalyzed a-mono-borylation of a diverse series of pyridines is reported, affording a {valuable|beneficial|useful|worthwhile|precious|important} precursor for cross-coupling reactions. Experimental and theoretical mechanistic {evidence|proof} {support|assistance|help} the formation of a C-H activated η2-lanthanide-azine {complex|complicated}, followed by intermolecular a-mono-borylation {via|by way of|through|by means of} σ-bond metathesis. Notably, varying the lanthanide identity and substrate electronics promotes chemodivergence {of the|from the|in the|on the|with the|of your} catalytic selectivity: smaller/more electrophilic lanthanide3+ ions and electron-rich substrates favor selective a-C-H functionalization, whereas larger/less electrophilic lanthanide3+ 1 ions and electron poor substrates favor selective B-N bond-forming 1,2-dearomatization. Such organolanthanide series catalytic chemodivergence is, to our {knowledge|understanding|information|expertise|know-how}, unprecedented. 1831130-33-6 Data Sheet Methyl 4-chloro-3-oxobutanoate uses PMID:24563649
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