In-situ noncovalent interaction of ammonium ion enabled C–H bond functionalization of polyethylene glycols

Zongnan Zhang, Xueli Lv, Xin Mu, Mengyao Zhao, Sichang Wang, Congyu Ke, Shujiang Ding (), Dezhong Zhou (), Minyan Wang () and Rong Zeng ()
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Zongnan Zhang: Xi’an Jiaotong University
Xueli Lv: Nanjing University
Xin Mu: Xi’an Jiaotong University
Mengyao Zhao: Xi’an Shiyou University
Sichang Wang: Xi’an Shiyou University
Congyu Ke: Xi’an Shiyou University
Shujiang Ding: Xi’an Jiaotong University
Dezhong Zhou: Xi’an Jiaotong University
Minyan Wang: Nanjing University
Rong Zeng: Xi’an Jiaotong University

Nature Communications, 2024, vol. 15, issue 1, 1-10

Abstract: Abstract The noncovalent interactions of ammonium ion with multidentate oxygen-based host has never been reported as a reacting center in catalytic reactions. In this work, we report a reactivity enhancement process enabled by non-covalent interaction of ammonium ion, achieving the C–H functionalization of polyethylene glycols with acrylates by utilizing photoinduced co-catalysis of iridium and quinuclidine. A broad scope of alkenes can be tolerated without observing significant degradation. Moreover, this cyano-free condition respectively allows the incorporation of bioactive molecules and the PEGylation of dithiothreitol-treated bovine serum albumin, showing great potentials in drug delivery and protein modification. DFT calculations disclose that the formed α-carbon radical adjacent to oxygen-atom is reduced directly by iridium before acrylate addition. And preliminary mechanistic experiments reveal that the noncovalent interaction of PEG chain with the formed quinuclidinium species plays a unique role as a catalytic site by facilitating the proton transfer and ultimately enabling the transformation efficiently.

Date: 2024
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DOI: 10.1038/s41467-024-48584-8

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