Synlett 2017; 28(15): 1857-1866
DOI: 10.1055/s-0036-1590841
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© Georg Thieme Verlag Stuttgart · New York

Recent Advances in Ring-Opening Polymerization of O-Carboxyanhydrides

Quanyou Fenga, b, Yongliang Zhongb, Linghai Xie*a, Rong Tong*b
  • aCenter for Molecular Systems and Organic Devices, Institute of Optoelectronic Materials, Key Laboratory for Organic Electronics and Information Displays & Institute of Advanced Materials, Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing University of Posts and Telecommunications, 9 Wenyuan Road, Nanjing 210023, P. R. of China   Email: iamlhxie@njupt.edu.cn
  • bDepartment of Chemical Engineering, Virginia Polytechnic Institute and State University, 635 Prices Fork Road, Blacksburg, VA, 24061, USA   Email: rtong@vt.edu
This work was supported by start-up funding from Virginia Polytechnic Institute and State University. Q.F. acknowledges support from National Natural Science Foundation of China (21504047), Natural Science Foundation of Jiangsu Province (BK20150834), Nanjing University of Posts and Telecommunications Scientific Foundation NUPTSF (NY214179).
Further Information

Publication History

Received: 06 May 2017

Accepted after revision: 21 June 2017

Publication Date:
03 August 2017 (eFirst)

Abstract

Poly(α-hydroxy acids) are important biodegradable polymers with wide applications. Recently O-carboxyanhydrides (OCAs) have emerged as promising monomer equivalents of lactides to synthesize poly(α-hydroxy acids). We will highlight recent advances in controlled ring-opening polymerization of OCAs catalyzed by organocatalysts, enzymes, or organometallic complexes.

1 Introduction

2 Organocatalysts for O-Carboxyanhydride Polymerization

2.1 Synthesis of O-Carboxyanhydride Monomers

2.2 Ring-Opening Polymerization of O-Carboxyanhydrides Catalyzed by 4-Dimethylaminopyridine

2.3 Epimerization in the Ring-Opening Polymerization of O-Carboxyanhydrides Catalyzed by the Pyridine Base

2.4 N-Heterocyclic Carbenes for Ring-Opening Polymerization of O-Carboxyanhydrides

3 Enzymes for O-Carboxyanhydride Polymerization

4 Organometallic Catalysts for O-Carboxyanhydride Polymerization

4.1 Early Efforts

4.2 Ring-Opening Polymerization Catalyzed by Zn Complexes

4.3 Photoredox Ring-Opening Polymerization Catalyzed by Zn/Ni Complexes

5 Conclusion and Perspective