PPh3-Assisted Esterification of Acyl Fluorides with Ethers via C(sp3)-O Bond Cleavage Accelerated by TBAT

被引：9

作者：

Wang, Zhenhua ^{[1
]}

Wang, Xiu ^{[1
]}

Nishihara, Yasushi ^{[2
]}

机构：

[1] Okayama Univ, Grad Sch Nat Sci & Technol, Kita Ku, 3-1-1 Tsushimanaka, Okayama 7008530, Japan

[2] Okayama Univ, Res Inst Interdisciplinary Sci, Kita Ku, 3-1-1 Tsushimanaka, Okayama 7008530, Japan

来源：

CATALYSTS | 2019年 / 9卷 / 07期

关键词：

Acyl fluorides; cyclopentyl methyl ether (CPME); tetrabutylammonium difluorotriphenysilicate (TBAT); carbon-oxygen bond cleavage; esterification; ARYL ALKYL ETHERS; METHYL ETHERS; ESTERS; PALLADIUM; IODIDE; DEMETHYLATION; CHLORIDES; SODIUM; COPPER; ACID;

D O I：

10.3390/catal9070574

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

We describe the (triphenylphosphine (PPh3)-assisted methoxylation of acyl fluorides with cyclopentyl methyl ether (CPME) accelerated by tetrabutylammonium difluorotriphenysilicate (TBAT) via regiospecific C-OMe bond cleavage. Easily available CPME is utilized not only as the solvent, but a methoxylating agent in this transformation. The present method is featured by C-O and C-F bond cleavage under metal-free conditions, good functional-group tolerance, and wide substrate scope. Mechanistic studies revealed that the radical process was not involved.

引用

页数：12

共 50 条

[21] Palladium(ii)-catalyzed oxidative C(sp3)-P bond formation via C(sp3)-H bond activation
Chen, Lijin
Zhou, Zhenfei
Zhang, Saifei
Li, Xiaoqian
Ma, Xuebing
Dong, Jiaxing
CHEMICAL COMMUNICATIONS, 2019, 55 (91) : 13693 - 13696
[22] Dimethylbut-2-ynedioate mediated esterification of acids via sp3 C-N bond cleavage of benzylic tertiary amines
Shen, Hao
Lu, Xing
Jiang, Ke-Zhi
Yang, Ke-Fang
Lu, Yixin
Zheng, Zhan-Jiang
Lai, Guo-Qiao
Xu, Li-Wen
TETRAHEDRON, 2012, 68 (43) : 8916 - 8923
[23] Pd-Catalyzed Ring-Opening Polymerization of Cyclobutanols through C(sp3)-C(sp3) Bond Cleavage
Parra-Garcia, Sergio
Saura-Llamas, Isabel
Bautista, Delia
Gil-Rubio, Juan
Garcia-Lopez, Jose-Antonio
MACROMOLECULES, 2024, 57 (14) : 6577 - 6582
[24] Dual transition metal electrocatalysis enables selective C(sp3)-C(sp3) bond cleavage and arylation of cyclic alcohols
Li, Weixiang
Zhang, Ruipu
Zhou, Naifu
Lu, Jiaqing
Fu, Niankai
CHEMICAL COMMUNICATIONS, 2024, 60 (82) : 11714 - 11717
[25] Direct oxidative coupling of thiols and benzylic ethers via C(sp3)-H activation and C-O cleavage to lead thioesters
Feng, J.
Lv, M. -F.
Lu, G. -P.
Cai, C.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (03) : 677 - 681
[26] Co-Catalyzed C(sp3)-C(sp2) bond cleavage via hydrogen atom transfer
Zhou, Bingqing
Tian, Di
An, Jinglin
Zhou, Yalan
Yan, Rui
Song, Hao
Liu, Xiao-Yu
Qin, Yong
ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (08) : 2135 - 2140
[27] Rhodium-catalyzed intramolecular carbosilylation of alkynes via C(sp3)-Si bond cleavage
Yang, Qi
Liu, Liang
Chi, Yue
Hao, Wei
Zhang, Wen-Xiong
Xi, Zhenfeng
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (05): : 860 - 863
[28] Palladium-Catalyzed Fluoroalkylation via C(sp3)-S Bond Cleavage of Vinylsulfonium Salts
He, Yuan
Huang, Zilong
Ma, Juan
Huang, Fei
Lin, Jie
Wang, Hongmei
Xu, Bao-Hua
Zhou, Yong-Gui
Yu, Zhengkun
ORGANIC LETTERS, 2021, 23 (15) : 6110 - 6114
[29] Trifluoromethylation of Carbonyl and Unactivated Olefin Derivatives by C(sp3)-C Bond Cleavage
Cong, Fei
Mega, Riccardo S.
Chen, Jinhong
Day, Craig S.
Martin, Ruben
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (15)
[30] Ni-Catalyzed Regioselective Alkylarylation of Vinylarenes via C(sp3)-C(sp3)/C(sp3)-C(sp2) Bond Formation and Mechanistic Studies
Shekhar, K. C.
Dhungana, Roshan K.
Shrestha, Bijay
Thapa, Surendra
Khanal, Namrata
Basnet, Prakash
Lebrun, Robert W.
Giri, Ramesh
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (31) : 9801 - 9805

← 1 2 3 4 5 →