Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 19, Pages 6136-6139Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b02272
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Funding
- NSF [CHE-1301409, RII-1330840]
- ND EPSCoR
- NIH National Center for Research Resources [2P20 RR015566]
- NSF-CRIF [CHE-0946990]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1301409] Funding Source: National Science Foundation
- Office Of The Director
- Office of Integrative Activities [1330840] Funding Source: National Science Foundation
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A Modular and atom-efficient synthesis of 2-aza-1,3-butadiene:,derivatives, has been developed via nickel-Catalyzed intermolecular coupling between internal alkynes. and aromatic N-H ketimines. This novel alkyne hydroimination process, is promoted by a catalyst system of a Ni(0) precursor ([Ni(cod)(2)]), N-heterocyclic carbene (NHC) ligand (IPr), and Cs2CO3 additive. The exclusive formation of (Z)-enamine stereoisoimers is Consistent with a proposed anti-iminometalation of alkyne by pi-complexation with Ni(0) and subsequent attack by the N-H ketimine nucleophile. An NHC-ligated,Ni(0) pi-imine complex, [(IPr)(eta(1)-HN=CPh2)(eta(2)-HN=CPh2)], Was independently synthesized and displayed improved re-activity as the catalyst precursor.
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