Cited by 178biodegradable polymer synthesis and propertiesOrganometallic Complex Synthesis and CatalysisAdvanced Polymer Synthesis and Characterization

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Metal‐Size Influence in Iso‐Selective Lactide Polymerization

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Bakewell, Clare, White, Andrew J. P., Long, Nicholas J., Williams, Charlotte K.·2014·Angewandte Chemie International Edition

DOI 10.1002/anie.201403643PMC PMC4499264

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Abstract

Iso‐selective initiators for the ring‐opening polymerization (ROP) of rac‐lactide are rare outside of Group 13. We describe the first examples of highly iso‐selective lutetium initiators. The phosphasalen lutetium ethoxide complex shows excellent iso‐selectivity, with a Pi value of 0.81–0.84 at 298 K, excellent rates, and high degrees of polymerization control. Conversely, the corresponding La derivative exhibits moderate heteroselectivity (Ps=0.74, 298 K). Thus, the choice of metal center is shown to be crucial in determining the level and mode of stereocontrol. The relative order of rates for the series of complexes is inversely related to metallic covalent radius: that is, La>Y>Lu.

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Figure 1 The structure of iso-selective yttrium phosphasalen complexes A and B[8c] and a homochiral lanthanide complex C, reported by Arnold et al.[8a]CC BY · PubMed Central

Scheme 1 Synthesis and structure of initiators 1–3. a) Reaction conditions: 1) KN(SiMe3)2 (5 equiv), THF, 2 h, 298 K; 2) LuCl3 or LaCl3, THF, 4 h, 298 K; 3) KOR, THF, 4 h, 298 K.CC BY · PubMed Central

Figure 2 Schematic representation of the single-crystal X-ray structures of complex 1 (M=Lu, R=tBu), 2 (M=Lu, R=Et) and 3 (molecules A and B, M=La, R=tBu).CC BY · PubMed Central

Figure 3 Plot of kobs value versus [2]. Polymerization conditions: [LA]0=1 m, [2]=2–5 mm,THF, 298 K. Average errors: 1–8 %.CC BY · PubMed Central

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Authors: Bakewell, C., White, A. J. P., Long, N. J., & Williams, C. K.
Affiliations: Imperial College London (GB)
Corresponding author: Long, Nicholas J.
Williams, Charlotte K.
ORCID: Bakewell, Clare
White, Andrew J. P.
Long, Nicholas J.
Williams, Charlotte K.
Venue: Angewandte Chemie International Edition
Publisher: Wiley
Published: 2014-07-07
Volume: 53
Issue: 35
Pages: 9226-9230
ISSN: 1433-7851 (ISSN-L)
1521-3773
DOI: 10.1002/anie.201403643
PMC: PMC4499264
OpenAlex: W2161922448
Cited by: 178
References: 72
Citations by year: 2026: 3 · 2025: 2 · 2024: 4 · 2023: 4 · 2022: 10 · 2021: 9 · 2020: 16 · 2019: 21 · 2018: 23 · 2017: 31 · 2016: 27 · 2015: 23 · 2014: 4
FWCI: 10.74
Type: journal article
Language: en
Open access: green
www.ncbi.nlm.nih.gov
Licence: cc-by
onlinelibrary.wiley.com/termsAndConditions#vor (vor)
Locations: Angewandte Chemie International Edition (publishedVersion)
PubMed Central (publishedVersion, cc-by)
PubMed (publishedVersion)
Spiral (Imperial College London) (submittedVersion, other-oa)
Funders: Engineering and Physical Sciences Research Council (EP/C544838/1, EP/K035274/1, EP/C544846/1)
Topics: Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
Physical Sciences › Chemistry › Organic Chemistry › Organometallic Complex Synthesis and Catalysis
Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
Keywords: rac-lactide, stereocontrol, polymerization rate, degree of polymerization control

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Metal‐Size Influence in Iso‐Selective Lactide Polymerization

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