Journal of the American Chemical Society
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CONTENT
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Supporting Information. Additional experimental procedures,
characterization data, and spectra of new compounds.
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Duchateau, R. Macromolecules 2012, 45, 1770–1776. (g) Darensbourg,
D. J.; Poland, R. R.; Escobedo, C. Macromolecules 2012, 45, 2242–2248.
(h) Hosseini Nejad, E.; Paoniasari, A.; Koning, C. E.; Duchateau, R.
Polym. Chem. 2012, 3, 1308–1313. (i) Harrold, N. D.; Li, Y.; Chisholm,
M. H. Macromolecules 2013, 46, 692-698. (j) Bernard, A.; Chatterjee, C.;
Chisholm, M. H. Polymer 2013, 54, 2639-2646. (k) Liu, J.; Bao, Y.-Y.; Liu,
Y.; Ren, W.-M.; Lu, X.-B. Polym. Chem. 2013, 4, 1439–1444. (l) Van Zee,
N. J.; Coates, G. W. Chem. Commun. 2014, 50, 6322–6325. (m) Saini, P.
K.; Romain, C.; Zhu, Y.; Williams, C. K. Polym. Chem. 2014, 5, 6068-
6075. (n) Longo, J. M.; DiCiccio, A. M.; Coates, G. W. J. Am. Chem. Soc.
2014, 136, 15897-15900. (o) Liu, D.-F.; Zhu, L.-Q., Wu, J.; Wu, L.-Y.; Lu,
X.-Q. RSC Adv. 2015, 5, 3854-3859. (p) Van Zee, N. J.; Coates, G. W.
Angew. Chem. Int. Ed. 2015, 54, 2665-2668. (q) Paul, S.; Zhu, Y.;
Romain, C.; Brooks, R.; Saini, P. K.; Williams, C. K. Chem. Commun.
2015, 51, 6459-6479. (r) Mundil, R.; Host’alek, Z.; Sedenkova, I.; Merna,
J. Macromol. Res. 2015, 23, 161-166. (s) Baumgartner, R.; Song, Z.;
Zhang, Y.; Cheng, J. Polym. Chem. 2015, 6, 3586-3590. (t) Han, B.;
Zhang, L.; Liu, B.; Dong, X.; Kim, I.; Duan, Z.; Theato, P. Macromolecules
2015, 48, 3431-3437. (u) Si, G.; Zhang, L.; Han, B.; Duan, Z.; Li, B.;
Dong, J.; Li, X.; Liu, B. Polym. Chem. 2015, 6, 6372-6377. (v) Zhu, Y.;
Romain, C.; Williams, C. K. J. Am. Chem. Soc. 2015, 137, 12179-12182.
Liu, D.; Zhang, Z.; Zhang, X.; Lue, X. Aust. J. Chem. 2016, 69, 47-55. (w)
Van Zee, N. J.; Sanford, M. J.; Coates, G. W. J. Am. Chem. Soc. 2016, 138,
2755-2761.
(10) (a) Coates, G. W.; Moore, D. R. Angew. Chem. Int. Ed. 2004, 43,
6618-6639. (b) Darensbourg, D. J. Chem. Rev. 2007, 107, 2388-2410. (c)
Kember, M. R.; Buchard, A.; Williams, C. K. Chem. Commun. 2010, 47,
141-163.
(11) (a) Allen, S. D.; Moore, D. R.; Lobkovsky, E. B.; Coates, G. W. J.
Am. Chem. Soc. 2002, 124, 14284-14285. (b) Darensbourg, D. J.;
Yarbrough, J. C. J. Am. Chem. Soc. 2002, 124, 6335-6342. (c) Eberhardt,
R.; Allmendinger, M.; Rieger, B. Macromol. Rapid Commun. 2003, 24,
194-196.
(12) (a) Cohen, C. T.; Chu, T.; Coates, G. W. J. Am. Chem. Soc. 2005,
127, 10869-10878. (b) Cohen, C. T.; Coates, G. W. J. Polym. Sci., Part A:
Polym. Chem. 2006, 44, 5182–5191. (c) Nakano, K.; Hashimoto, S.;
Nakamura, M.; Kamada, T.; Nozaki, K. Angew. Chem., Int. Ed. 2011, 50,
4868–4871. (d) Ren, W.-M.; Liu, Y.; Wu, G.-P.; Liu, J.; Lu, X.-B. J. Polym.
Sci., Part A: Polym. Chem. 2011, 49, 4894-4901. (e) Lu, X.B.; Ren, W.-
M.; Wu, G. P. Acc. Chem. Res. 2012, 45, 1721-1753.
(13) (a) Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N.
Science, 1997, 277, 936–938. (b) Jacobsen, E. N. Acc. Chem. Res. 2000,
33, 421–431.
AUTHOR INFORMATION
Corresponding Author
Present Addresses
† Verily Life Sciences, 1600 Amphitheatre Parkway, Mountain View,
CA 94043
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ACKNOWLEDGMENTS
We thank the Center for Sustainable Polymers, an NSF Center for
Chemical Innovation (CHE-1413862) for financial support. A.M.D.
acknowledges the NSF IGERT program for financial support. J.M.L.
acknowledges the NSF GRFP (DGE-1144153) for financial support.
We acknowledge Catherine DeBlase for assistance with the
electrochemistry experiments.
REFERENCES
(1) (a) Vaughan, A.; Davis, D. S.; Hagadorn, J. R. Industrial Catalysts
for Alkene Polymerization. In Polymer Science: A Comprehensive
Reference; Matyjaszewski, K.; Möller, M.; Eds.; Elsevier: Amsterdam,
2012; Vol. 3, p 661. (b) U. S. Resin Production and Sales 2013 vs. 2012.
Statistics/Production-and-Sales-Data-by-Resin.pdf (accessed Mar 5,
2016).
(2) (a) Peacock, A. Handbook of Polyethylene: Structures, Properties,
and Applications; CRC Press: New York, 2000. (b) Resconi, L.; Cavallo,
L.; Fait, A.; Piemontesi, F. Chem. Rev. 2000, 100, 1253–1345.
(3) (a) Gibson, V. C.; Spitzmesser, S. K. Chem. Rev. 2003, 103, 283–
315. (b) Coates, G. W.; Hustad, P. D.; Reinartz, S. Angew. Chem. Int. Ed.
2002, 41, 2236–2257. (c) Domski, G. J.; Rose, J. M.; Coates, G. W.; Bolig,
A. D.; Brookhart, M. Prog. Polym. Sci. 2007, 32, 30–92.
(4) (a) Boffa, L. S.; Novak, B. M. Chem. Rev. 2000, 100, 1479–1493.
(b) Chung, T. C. M. Functionalization of Polyolefins; Academic Press:
London, 2002. (c) Nakamura, A.; Ito, S.; Nozaki, K. Chem. Rev. 2009,
109, 5215–5244.
(5) (a) Polyesters, Thermoplastic. Kirk-Othmer Encyclopedia of
Chemical Technology, 5th ed.; Wiley: New York, 2004; Vol. 20 pp. 34–95.
(b) Polyesters, Unsaturated. Kirk-Othmer Encyclopedia of Chemical
Technology, 5th ed.; Wiley: New York, 2004; Vol. 20 pp. 96–130.
(6) (a) Coates, G. W. Chem. Rev. 2000, 100, 1223-1252. (b)
Corradini, P.; Guerra, G.; Cavallo, L. Acc. Chem. Res. 2004, 37, 231-241.
(c) Stereoselective Polymerization with Single-Site Catalysts; Baugh, L. S.;
Canich, J. A. M.; Eds.; CRC Press/Taylor & Francis Group: Boca Raton,
Floride, 2008.
(14) (a) Cohen, C. T.; Thomas, C. M.; Peretti, K. L.; Lobkovsky, E. B.;
Coates, G. W. Dalton Trans. 2006, 237-249. (b) Lu, X.-B.; Liang, B.;
Zhang, Y.-J.; Tian, Y.-Z.; Wang, Y.-M.; Bai, C.-X.; Wang, H.; Zhang, R. J.
Am. Chem. Soc. 2004, 126, 3732-3733.
(15) This is a modified procedure that differs from literature routes that
use AgNO3 for oxidation.
(16) Qin, Z.; Thomas, C. M.; Lee, S.; Coates, G. W. Angew. Chem. Int.
Ed. 2003, 42, 5484-5487.
(7) Odian, G. Principles of Polymerization, 4th ed.; John Wiley & Sons:
New Jersey, 2004; pp. 39-197.
(17) Selected papers that discuss these phenomena: (a) Nishinaga, A.;
Tajima, K.; Speiser, B.; Eiczhorn, E.; Rieker, A.; Ohya-Nishiguchi, H.;
Ishizu, K. Chem. Lett. 1991, 8, 1403–1406. (b) Schenk, K. J.; Meghdadi,
S.; Amirnasr, M.; Habibi, M. H.; Amiri, A.; Salehi, M.; Kashi, A.
Polyhedron 2007, 26, 5448–5457. (c) Thomas, F.; Arora, H.; Philouze,
C.; Jarjayes, O. Inorg. Chim. Acta 2010, 363, 3122–3130. (d) Zhuang, X.;
Oyaizu, K.; Niu, Y.; Koshika, K.; Chen, X.; Nishide, H. Macromol. Chem.
Phys. 2010, 211, 669–676. (e) Kochem, A.; Kanso, H.; Baptiste, B.; Arora,
H.; Philouze, C.; Jarjayes, O.; Vezin, H.; Luneau, D.; Orio, M.; Thomas, F.
Inorg. Chem. 2012, 51, 10557–10571. (f) Kochem, A.; Chiang, L.;
Baptiste, B.; Philouze, C.; Leconte, N.; Jarjayes, O.; Storr, T.; Thomas, F.
Chem. Eur. J. 2012, 18, 14590–14593. (g) Kurahashi, T.; Fujii, H. Inorg.
Chem. 2013, 52, 3903–3910. (h) Chiang, L.; Allan, L. E. N.; Alcantara, J.;
(8) (a) Kamber, N. E.; Jeong, W.; Waymouth, R. M.; Pratt, R. C.;
Lohnmeijer, B. G. G.; Hedrick, J. L. Chem. Rev. 2007, 107, 5813–5840.
(b) Jérôme, C.; Lecomte, P. Adv. Drug Delivery Rev. 2008, 60, 1056–
1076. (c) Stanford, M. J.; Dove, A. P. Chem. Soc. Rev. 2010, 39, 486–494.
(9) (a) Jeske, R. C.; DiCiccio, A. M.; Coates, G. W. J. Am. Chem. Soc.
2007, 129, 11330–11331. (b) Jeske, R. C.; Rowley, J. M.; Coates, G. W.
Angew. Chem., Int. Ed. 2008, 47, 6041–6044. (c) Huijser, S.; Hosseini
Nejad, E.; Sablong, R.; Jong, C. D.; Koning, C. E.; Duchateau, R.
Macromolecules 2011, 44, 1132–1139. (d) DiCiccio, A. M.; Coates, G.
W. J. Am. Chem. Soc. 2011, 133, 10724–10727. (e) Robert, C.; de
Montigny, F.; Thomas, C. M. Nat. Commun. 2011, 2, 1596/1-1596/6. (f)
Hosseini Nejad, E.; van Melis, C. G. W.; Vermeer, T. J.; Koning, C. E.;
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