Journal
ACS MACRO LETTERS
Volume 5, Issue 8, Pages 982-986Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsmacrolett.6b00527
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Funding
- NSF CAREER Award [CHE 1554830]
- University of Rhode Island
- NSF [1531963]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1554830, 1531963] Funding Source: National Science Foundation
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A new class of H-bond donating ureas was developed for the ring-opening polymerization (ROP) of lactone monomers, and they exhibit dramatic rate acceleration versus previous H-bond mediated polymerization catalysts. The most active of these new catalysts, a tris-urea H-bond donor, is among the most active organocatalysts known for ROP, yet it retains the high selectivity of H-bond mediated organocatalysts. The urea cocatalyst, along with an H-bond accepting base, exhibits the characteristics of a living ROP, is highly active, in one case, accelerating a reaction from days to minutes, and remains active at low catalyst loadings. The rate acceleration exhibited by this H-bond donor occurs for all base cocatalysts examined. A mechanism of action is proposed, and the new catalysts are shown to accelerate small molecule transesterifications versus currently known monothiourea catalysts. It is no longer necessary to choose between a highly active or highly selective organocatalyst for ROP.
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