Chemical Upcycling of Waste Poly(bisphenol A carbonate) to 1,4,2-Dioxazol-5-ones and One-Pot C-H Amidation

被引：13

作者：

Jung, Hyun Jin ^{[1
,2
]}

Park, Sora ^{[1
,2
]}

Lee, Hyun Sub ^{[1
,2
]}

Shin, Hyun Gyu ^{[1
,2
]}

Yoo, Yeji ^{[1
,2
]}

Baral, Ek Raj ^{[1
,2
]}

Lee, Jun Hee ^{[3
]}

Kwak, Jaesung ^{[4
]}

Kim, Jeung Gon ^{[1
,2
]}

机构：

[1] Jeonbuk Natl Univ, Dept Chem, Jeonju 54896, South Korea

[2] Jeonbuk Natl Univ, Res Inst Phys & Chem, Jeonju 54896, South Korea

[3] Dongguk Univ, Dept Adv Mat Chem, Gyeongju 38066, South Korea

[4] Korea Res Inst Chem Technol KRICT, Infect Dis Therapeut Res Ctr, Deajeon 34114, South Korea

来源：

CHEMSUSCHEM | 2021年 / 14卷 / 19期

基金：

新加坡国家研究基金会;

关键词：

C-H amidation; chemical recycling; dioxazolone; polycarbonate; upcycling; BISPHENOL-A; POLYCARBONATE; DEPOLYMERIZATION; ALCOHOLYSIS; HYDROLYSIS; PYROLYSIS; BIOMASS; MILD;

D O I：

10.1002/cssc.202100885

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chemical upcycling of poly(bisphenol A carbonate) (PC) was achieved in this study with hydroxamic acid nucleophiles, giving rise to synthetically valuable 1,4,2-dioxazol-5-ones and bisphenol A. Using 1,5,7-triazabicyclo[4.4.0]-dec-5-ene (TBD), non-green carbodiimidazole or phosgene carbonylation agents used in conventional dioxazolone synthesis were successfully replaced with PC, and environmentally harmful bisphenol A was simultaneously recovered. Assorted hydroxamic acids exhibited good-to-excellent efficiencies and green chemical features, promising broad synthetic application scope. In addition, a green aryl amide synthesis process was developed, involving one-pot depolymerization from polycarbonate to dioxazolone followed by rhodium-catalyzed C-H amidation, including gram-scale examples with used compact discs.

引用

页码：4301 / 4306

页数：6

共 50 条

[21] C-C Bond Cleavage Initiated Cascade Reaction of β-Enaminones: One-Pot Synthesis of 5-Hydroxy-1H-pyrrol-2(5H)-ones
Chen, Ting
Zheng, Xiujuan
Wang, Wenhua
Feng, Yadong
Wang, Yanyun
Shen, Jinhai
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (03): : 2917 - 2928
[22] Palladium-catalyzed double C-H activation: one-pot synthesis of benzo[c] pyrazolo[1,2-a]-cinnolin-1-ones from 5-pyrazolones and aryl iodides
Fan, Zhoulong
Wu, Kui
Xing, Li
Yao, Qizheng
Zhang, Ao
CHEMICAL COMMUNICATIONS, 2014, 50 (14) : 1682 - 1684
[23] Diphenylphosphoryl Azide (DPPA)-Mediated One-Pot Synthesis of Oxazolo[4,5-c][1,8]naphthyridin-4(5 H)-ones, Oxazolo[4,5-c]quinoline-4(5 H)-ones, and Tosyloxazol-5-yl Pyridines
Tangella, Yellaiah
Manasa, Kesari Lakshmi
Sathish, Manda
Alarifi, Abdullah
Kamal, Ahmed
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (07) : 898 - 906
[24] Ligand-Free Copper-Manganese Spinel Oxide-Catalyzed Tandem One-Pot C-H Amidation and N-Arylation of Benzylamines: A Facile Access to 2-Arylquinazolin-4(3H)-ones
Sharma, Rohit
Vishwakarma, Ram A.
Bharate, Sandip B.
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (19) : 3027 - 3033
[25] Cascade One-Pot Method To Synthesize Isoquinolin-1(2H)-ones with α-Bromo Ketones and Benzamides via Pd-catalyzed C-H Activation
Xie, Caixia
Dai, Zhen
Niu, Yadi
Ma, Chen
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (04): : 2317 - 2323
[26] Synthesis of pyrazolo[1,5-a] quinoxalin-4(5H)-ones via one-pot amidation/N-arylation reactions under transition metal-free conditions
Wiethan, Carson
Franceschini, Steffany Z.
Bonacorso, Helio G.
Stradiotto, Mark
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (37) : 8721 - 8727
[27] A NOVEL ONE-POT SYNTHESIS OF SUBSTITUTED-1H-PYRIDAZIN-4-ONES AND THEIR CONVERSION TO SUBSTITUTED-2H-PYRAZOLO[4,3-C]PYRIDAZINES
PATEL, HV
PANDEY, SP
FERNANDES, PS
VYAS, KA
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1991, 30 (10): : 932 - 935
[28] Efficient one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones from aromatic aldehydes and their one-pot oxidation to quinazolin-4(3H)-ones catalyzed by Bi(NO3)3•5H2O: Investigating the role of the catalyst
Mohammadpoor-Baltork, Iraj
Khosropour, Ahmad R.
Moghadam, Majid
Tangestaninejad, Shahram
Mirkhani, Valiollah
Baghersad, Saeid
Mirjafari, Arsalan
COMPTES RENDUS CHIMIE, 2011, 14 (10) : 944 - 952
[29] DABCO CONTAINING ACIDIC POLY( IONIC LIQUID): AN EFFICIENT CATALYST FOR THE ONE-POT PREPARATION OF 2,3-DIHYDROQUINAZOLINE-4(1H)-ONES
Mohammadi, Mohammad Kazem
Saghanezhad, Seyyed Jafar
Razzaghi-asl, Nima
BULLETIN OF THE CHEMICAL SOCIETY OF ETHIOPIA, 2017, 31 (03) : 535 - 544
[30] One-pot B(C6F5)3 catalyzed cascade synthesis of 2-substituted-2,3-dihydroquinazolin-4(1H)-ones
Shinde, Achut R.
Mane, Yogesh D.
Muley, Dnyanoba B.
SYNTHETIC COMMUNICATIONS, 2020, 50 (01) : 33 - 40

← 1 2 3 4 5 →