Synthesis of acetyl-substituted tetrahydrobenzofuran and tetrahydronaphthalene via cascade Diels-Alder cycloadditions and dehydration of renewable furanics

doi:10.1016/j.apcata.2018.11.004

	Synthesis of acetyl-substituted tetrahydrobenzofuran and tetrahydronaphthalene via cascade Diels-Alder cycloadditions and dehydration of renewable furanics
	Xia, Zhi; Marri, Mahender Reddy; Zhang, Xiaoqiang; Yan, Peifang; Ramineni, Kishore; Huang, Tingyu; Balaga, Ravi; Zhang, Zongchao Conrad
刊名	APPLIED CATALYSIS A-GENERAL
	2019-01-25
卷号	570 页码:107-112
关键词	Diels-Alder reaction Dehydration Sn-Beta Bioderived products Furanics
ISSN号	0926-860X
DOI	10.1016/j.apcata.2018.11.004
通讯作者	Zhang, Zongchao Conrad(zczhang@yahoo.com)
英文摘要	A acetyl-substituted tetrahydrobenzofuran, 1-(4,5,6,7-tetrahydro-1-benzofuran-6-yl)ethenone (6-AcBZOF) and a acetyl-substituted tetrahydronaphthalene, 1-(1,2,3,4-tetrahydronaphthalen-2-yl)ethenone (2-AcTNAPH) were conveniently synthesized from renewable furanics by cascade Diels-Alder and dehydration reactions. The Diels-Alder cycloaddition of 4-(2-Furyl)-3-buten-2-one (4-FB) with ethylene followed by dehydration in presence of zeolites was studied. Sn grafted Beta zeolite exhibited high performance with 69% yield of 2-AcTNAPH starting from 4-FB. In this reaction, 6-AcBZOF was produced as intermediate. Further, it was found that this acetyl substituted tetrahydrobenzofuran could be formed in high yield, 86%, in the absence of catalyst. For the first time in the literature, we report the synthesis of a renewable acetyl-substituted tetrahydronaphthalene in high yield from biomass-derived 4-FB in a tandem approach. While a acetyl-substituted tetrahydrobenzofuran could be prepared without a catalyst, catalyst was essential for the successful synthesis of the acetyl-substituted tetrahydronaphthalene.
资助项目	Chinese Academy of Science President's International Fellowship Initiative[2016PT022] ; Chinese Government Thousand Talent program ; CAS/SAFEA International Partnership Program for Creative Research Teams
WOS关键词	BIOMASS-DERIVED DIMETHYLFURAN ; TEREPHTHALIC ACID ; O-QUINODIMETHANE ; ETHYLENE ; AROMATIZATION ; DERIVATIVES ; GENERATION ; CONVERSION ; CATALYSIS ; 2,5-DIMETHYLFURAN
WOS研究方向	Chemistry ; Environmental Sciences & Ecology
语种	英语
出版者	ELSEVIER SCIENCE BV
WOS记录号	WOS:000457661500011
资助机构	Chinese Academy of Science President's International Fellowship Initiative ; Chinese Academy of Science President's International Fellowship Initiative ; Chinese Government Thousand Talent program ; Chinese Government Thousand Talent program ; CAS/SAFEA International Partnership Program for Creative Research Teams ; CAS/SAFEA International Partnership Program for Creative Research Teams ; Chinese Academy of Science President's International Fellowship Initiative ; Chinese Academy of Science President's International Fellowship Initiative ; Chinese Government Thousand Talent program ; Chinese Government Thousand Talent program ; CAS/SAFEA International Partnership Program for Creative Research Teams ; CAS/SAFEA International Partnership Program for Creative Research Teams ; Chinese Academy of Science President's International Fellowship Initiative ; Chinese Academy of Science President's International Fellowship Initiative ; Chinese Government Thousand Talent program ; Chinese Government Thousand Talent program ; CAS/SAFEA International Partnership Program for Creative Research Teams ; CAS/SAFEA International Partnership Program for Creative Research Teams ; Chinese Academy of Science President's International Fellowship Initiative ; Chinese Academy of Science President's International Fellowship Initiative ; Chinese Government Thousand Talent program ; Chinese Government Thousand Talent program ; CAS/SAFEA International Partnership Program for Creative Research Teams ; CAS/SAFEA International Partnership Program for Creative Research Teams
内容类型	期刊论文
源URL	[http://cas-ir.dicp.ac.cn/handle/321008/166074]
专题	大连化学物理研究所_中国科学院大连化学物理研究所
通讯作者	Zhang, Zongchao Conrad
作者单位	Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian Natl Lab Clean Energy, 457 Zhongshan Rd, Dalian 116023, Peoples R China
推荐引用方式 GB/T 7714	Xia, Zhi,Marri, Mahender Reddy,Zhang, Xiaoqiang,et al. Synthesis of acetyl-substituted tetrahydrobenzofuran and tetrahydronaphthalene via cascade Diels-Alder cycloadditions and dehydration of renewable furanics[J]. APPLIED CATALYSIS A-GENERAL,2019,570:107-112.
APA	Xia, Zhi.,Marri, Mahender Reddy.,Zhang, Xiaoqiang.,Yan, Peifang.,Ramineni, Kishore.,...&Zhang, Zongchao Conrad.(2019).Synthesis of acetyl-substituted tetrahydrobenzofuran and tetrahydronaphthalene via cascade Diels-Alder cycloadditions and dehydration of renewable furanics.APPLIED CATALYSIS A-GENERAL,570,107-112.
MLA	Xia, Zhi,et al."Synthesis of acetyl-substituted tetrahydrobenzofuran and tetrahydronaphthalene via cascade Diels-Alder cycloadditions and dehydration of renewable furanics".APPLIED CATALYSIS A-GENERAL 570(2019):107-112.