Journal
ORGANOMETALLICS
Volume 37, Issue 24, Pages 4648-4663Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.organomet.8b00682
Keywords
-
Categories
Funding
- Spanish Ministerio de Economia y Competitividad [CTQ2015-69568-P]
- Fundacion Seneca [19890/GERM/1S]
Ask authors/readers for more resources
The palladation reactions of 2-heteroaromatic primary phenethylamines bearing a benzofuran and benzothiophene nuclei have been studied. We have assessed the reactivity of the corresponding dimeric six-membered palladacycles (arising from C-H metalation) toward neutral ligands and unsaturated species. The insertion reactions of isocyanides into the Pd-C bond of the aforementioned palladacycles allowed the isolation of the corresponding iminoacyl intermediates, which could later be decomposed to give the amidine derivatives containing these relevant heterocyclic cores. In contrast, the carbonylation and alkenylation reactions led to straightforward formation of lactams and alkenylated organic derivatives. Interestingly, an unusual hydrogen-bond-promoted E-to-Z isomerization equilibrium of the resulting olefins was observed. Furthermore, we have studied the conditions to perform the alkenylation of the N-Boc derivatives of these substrates in a catalytic fashion. All the organometallic complexes (arising from the C-H activation of the heteroaromatic cores and insertion of isocyanides) and organic products (arising from the decomposition reactions) have been fully characterized, including the X-ray crystal structures of several organometallic and organic derivatives.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available