Journal
ACS CATALYSIS
Volume 11, Issue 23, Pages 14677-14687Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c03871
Keywords
heterocycles; catalysis; 2-aminopyridines; cycloaddition; mechanism; iron
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Funding
- Vicki & Patrick F. Stone family
- National Science Foundation (NSF) [CHE-1352663]
- University of Utah [1C06RR017539-01A1]
- National Institutes of Health [3R01GM063540-17W1, 1S10OD25241-01]
- University of Utah
- NSF REU [1659579]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1659579] Funding Source: National Science Foundation
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The mechanistic investigation into the origins of regio- and chemoselectivities observed in iron/pyridine dialdimine (PDAI)-catalyzed intermolecular [2+2+2] cycloaddition reactions of terminal alkynes and cyanamides reveals the significant role of the hemilabile PDAI ligand in controlling the observed selectivity of the resultant products.
A mechanistic investigation into the origins of the regio- and chemoselectivities observed in iron/pyridine dialdimine (PDAI)-catalyzed intermolecular [2+2+2] cycloaddition reactions of terminal alkynes and cyanamides to yield substituted 2-amino-pyridines is reported. The combination of experimental and computational studies disclosed herein reveals the role of the hemilabile PDAI ligand as an important factor controlling the resultant product's observed regio- and chemoselectivity.
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