Journal
ACS CATALYSIS
Volume 7, Issue 7, Pages 4381-4385Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b01444
Keywords
nickel; catalysis; cross-coupling; amides; kinetic modeling
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Funding
- NIH-NIGMS [R01 GM117016]
- UCLA Gold Shield Alumnae
- University of California, Los Angeles
- National Science Foundation [DGE-1144087]
- Foote Family
- NSF [CHE-1048804]
- National Center for Research Resources [S10RR025631]
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Nickel-catalyzed coupling reactions provide exciting tools in chemical synthesis. However, most methodologies in this area require high catalyst loadings, which commonly range from 10-20 mol % nickel. Through an academic-industrial collaboration, we demonstrate that kinetic modeling can be used strategically to overcome this problem, specifically within the context of the Ni-catalyzed conversion of amides to esters. The successful application of this methodology to a multigram-scale coupling, using only 0.4 mol % Ni, highlights the impact of this endeavor.
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