Synthesis of γ-Lactones by TBAI-Promoted Intermolecular Carboesterification of Carboxylic Acids with Alkenes and Alcohols

被引:6
作者
Chen, Rongxiang [1 ]
Wang, Kai-Kai [1 ]
Wang, Zhan-Yong [1 ]
Miao, Changqing [1 ]
Wang, Doudou [1 ]
Zhang, An-an [2 ]
Liu, Lantao [2 ]
机构
[1] Xinxiang Univ, Coll Chem & Chem Engn, Xinxiang 453000, Henan, Peoples R China
[2] Shangqiu Normal Univ, Coll Chem & Chem Engn, Shangqiu 476000, Henan, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H; IODINE; FUNCTIONALIZATION; LACTONIZATION; ALKYLATION; EFFICIENT; CARBON;
D O I
10.1021/acs.joc.9b02568
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel tetrabutylammonium iodide (TBAI)-promoted three-component reaction of carboxylic acid with alkene and alcohol has been developed, which represents facile and straightforward access to polysubstituted gamma-lactone skeletons in moderate-to-good yields. This methodology is distinguished by the use of a commercial catalyst and readily available starting materials, wide substrate scope, and operational simplicity. Mechanistic studies suggested that this transformation went through a radical process.
引用
收藏
页码:16068 / 16075
页数:8
相关论文
共 56 条
[1]   Paraconic acids -: The natural products from Lichen symbiont [J].
Bandichhor, R ;
Nosse, B ;
Reiser, O .
NATURAL PRODUCTS SYNTHESIS I: TARGETS METHODS CONCEPTS, 2005, 243 :43-72
[2]   Novel lactonization with phenonium ion participation induced by hypervalent iodine reagents [J].
Boye, AC ;
Meyer, D ;
Ingison, CK ;
French, AN ;
Wirth, T .
ORGANIC LETTERS, 2003, 5 (12) :2157-2159
[3]   Tetrabutylammonium Iodide-Promoted Acyloxylation-Peroxidation of Alkenes with Carboxylic Acid and tert -Butyl Hydroperoxide [J].
Chen, Rongxiang ;
Chen, Wei ;
Shen, Yuntao ;
Wang, Zhan-Yong ;
Dai, Wei ;
Wang, Kai-Kai ;
Liu, Lantao .
SYNLETT, 2019, 30 (14) :1708-1712
[4]   Combination of Tetrabutylammonium Iodide (TBAI) with tert-Butyl Hydroperoxide (TBHP): An Efficient Transition-Metal-Free System to Construct Various Chemical Bonds [J].
Chen, Rongxiang ;
Chen, Jijun ;
Zhang, Jie ;
Wan, Xiaobing .
CHEMICAL RECORD, 2018, 18 (09) :1292-1305
[5]   Copper- and Cobalt-Catalyzed Direct Coupling of sp3 α-Carbon of Alcohols with Alkenes and Hydroperoxides [J].
Cheng, Jun-Kee ;
Loh, Teck-Peng .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (01) :42-45
[6]   Quantification of Several 4-Alkyl Substituted γ-Lactones in Australian Wines [J].
Cooke, Rachel C. ;
Capone, Dimitra L. ;
van Leeuwen, Katryna A. ;
Elsey, Gordon M. ;
Sefton, Mark A. .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2009, 57 (02) :348-352
[7]   Direct lactone formation by using hypervalent Iodine(III) reagents with KBr via selective C-H abstraction protocol [J].
Dohi, Toshifumi ;
Takenaga, Naoko ;
Goto, Akihiro ;
Maruyama, Akinobu ;
Kita, Yasuyuki .
ORGANIC LETTERS, 2007, 9 (16) :3129-3132
[8]   Synthesis of γ-lactols, γ-lactones and 1,4-monoprotected succinaldehydes under moderately concentrated sunlight [J].
Dondi, Daniele ;
Protti, Stefano ;
Albini, Angelo ;
Carpio, Sonia Manas ;
Fagnoni, Maurizio .
GREEN CHEMISTRY, 2009, 11 (10) :1653-1659
[9]   Asymmetric Fluorolactonization with a Bifunctional Hydroxyl Carboxylate Catalyst [J].
Egami, Hiromichi ;
Asada, Junshi ;
Sato, Kentaro ;
Hashizume, Daisuke ;
Kawato, Yuji ;
Hamashima, Yoshitaka .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (32) :10132-10135
[10]   Flow Synthesis of Substituted γ- Lactones by Consecutive Photocatalytic/Reductive Reactions [J].
Fagnoni, Maurizio ;
Bonassi, Filippo ;
Palmieri, Alessandro ;
Protti, Stefano ;
Ravelli, Davide ;
Ballini, Roberto .
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (04) :753-758