scholarly journals Universal Chain-End Coupling Conditions for Brominated Polystyrenes, Polyacrylates, and Polymethacrylates

Processes ◽  
2021 ◽  
Vol 9 (6) ◽  
pp. 1001
Author(s):  
Joseph J. Andry ◽  
Jaenic J. Lee ◽  
Jessica Wu ◽  
Katherine Xia ◽  
Eric S. Tillman

Atom transfer radical coupling (ATRC), performed with or without radical traps, has allowed for high extents of coupling (Xc) for a variety of brominated polymers, yet structurally different polymeric chain ends require unique reagents and reaction conditions. Inspired by a similar study that focused on universal conditions for the controlled polymerization of different monomers using atom transfer radical polymerization (ATRP), this work focuses on developing a single set of conditions (or conditions with as little variation as possible) that will achieve extents of coupling greater than 80% or end-brominated chains of polystyrene (PSBr), poly(methyl methacrylate) (PMMABr), and poly(methyl acrylate) (PMABr). The radical traps α-phenyl-tert-butylnitrone (PBN), 2-methyl-2-nitrosopropane (MNP), and nitrosobenzene (NBz) were chosen in this study, along with copper catalysts, reducing agents, and nitrogen-based ligands. Ultimately, a single set of effective reaction conditions was identified with the only difference being the radical trap used: MNP was effective for coupling PSBr and PMABr while NBz was necessary to achieve similarly high extents of coupling for PMMABr.

2014 ◽  
Vol 47 (7) ◽  
pp. 2226-2232 ◽  
Author(s):  
Christopher J. Valente ◽  
Autumn M. Schellenberger ◽  
Eric S. Tillman

Polymer ◽  
2017 ◽  
Vol 127 ◽  
pp. 66-76 ◽  
Author(s):  
Jessica P. Wu ◽  
Ching W. Pan ◽  
Katherine E. Heiler ◽  
Megan E. Ching ◽  
Eric S. Tillman

Polymers ◽  
2014 ◽  
Vol 6 (11) ◽  
pp. 2737-2751 ◽  
Author(s):  
Elizabeth Carnicom ◽  
Jessica Abruzzese ◽  
Yacouba Sidibe ◽  
Kenneth Myers ◽  
Eric Tillman

2016 ◽  
Vol 217 (22) ◽  
pp. 2473-2482 ◽  
Author(s):  
Benjamin D. McFadden ◽  
Maya M. Arce ◽  
Elizabeth M. Carnicom ◽  
Julie Herman ◽  
Jessica Abrusezze ◽  
...  

2012 ◽  
Vol 1 (8) ◽  
pp. 1066-1070 ◽  
Author(s):  
Andrew F. Voter ◽  
Eric S. Tillman ◽  
Peter M. Findeis ◽  
Scott C. Radzinski

2019 ◽  
Author(s):  
Shiori Date ◽  
Kensei Hamasaki ◽  
Karen Sunagawa ◽  
Hiroki Koyama ◽  
Chikayoshi Sebe ◽  
...  

<div>We report here a catalytic, Markovnikov selective, and scalable synthetic method for the synthesis of saturated sulfur heterocycles, which are found in the structures of pharmaceuticals and natural products, in one step from an alkenyl thioester. Unlike a potentially labile alkenyl thiol, an alkenyl thioester is stable and easy to prepare. The powerful Co catalysis via a cobalt hydride hydrogen atom transfer and radical-polar crossover mechanism enabled simultaneous cyclization and deprotection. The substrate scope was expanded by the extensive optimization of the reaction conditions and tuning of the thioester unit.</div>


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