Friedel-Crafts cyclization of 1,1-difluoroalk-1-enes:: Synthesis of benzene-fused cyclic ketones via α-fluorocarbocations

被引：38

作者：

Ichikawa, J ^{[1
]}

Jyono, H

Kudo, T

Fujiwara, M

Yokota, M

机构：

[1] Univ Tokyo, Grad Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan

[2] Kyushu Inst Technol, Dept Appl Chem, Kitakyushu, Fukuoka 8048550, Japan

来源：

SYNTHESIS-STUTTGART | 2005年 / 01期

关键词：

Friedel-Crafts cyclization; difluoroalkene; bicyclic ketone; alpha-fluorocarbocation; fluoroalcohol solvent;

D O I：

10.1055/s-2004-834910

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,1-Difluoroalk-1-enes bearing a phenyl group at the C-3, -4, or -5 position, readily obtained from 2,2,2-trifluoroethyl p-toluenesulfonate, are treated with FSO3H.SbF5 to undergo Friedel-Crafts cyclization in (CF3)(2)CHOH. The cyclization takes place via alpha-fluorocarbocations. followed by spontaneous hydrolysis of the C-F bond to afford bicyclic ketones including a five, six, or seven-membered ring in good yield.

引用

页码：39 / 46

页数：8

共 50 条

[31] Synthesis of Pyrazolo[1,5-a]quinolines from 1-Aryl-5-styrylpyrazoles via Intramolecular Friedel-Crafts Reaction/Aerobic Oxidation
Moon, Hye Ran
Yu, Jin
Kim, Ko Hoon
Kim, Jae Nyoung
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2015, 36 (04) : 1189 - 1195
[32] Gold-catalyzed dehydrative Friedel-Crafts reaction and Nazarov cyclization sequence: an efficient synthesis of 1,3-diarylindenes from propargylic alcohols
Morita, Nobuyoshi
Miyamoto, Masazumi
Yoda, Akiyoshi
Yamamoto, Mari
Ban, Shintaro
Hashimoto, Yoshimitsu
Tamura, Osamu
TETRAHEDRON LETTERS, 2016, 57 (40) : 4460 - 4463
[33] Modern Friedel-Crafts chemistry.: Part-26.: A facile synthesis of trans-2-methyl-1-phenylindan via rearranged intramolecular cyclialkylati on of 1,2-biphenyl-2-methyl-2-propanol under Friedel-Crafts conditions
Khalaf, AA
Albar, HA
JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2004, 81 (06) : 518 - 521
[34] Transition-metal-free synthesis of triarylmethanes via Friedel-Crafts reactions of imidazo[1,2-a]pyridines with chlorohydrocarbon derivatives
Fu, Xinlei
Wu, Longhui
Guo, Xiaohua
Yang, Kai
Liu, Zhaowen
JOURNAL OF SAUDI CHEMICAL SOCIETY, 2024, 28 (04)
[35] Tandem Synthesis of 1,3-Disubstituted Naphthalenes via TfOH-Promoted Directed-Aldol and Friedel-Crafts Reactions
Li, Hongchen
Shan, Lidong
Min, Lin
Weng, Yunxiang
Wang, Xinyan
Hu, Yuefei
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (21): : 15011 - 15019
[36] Iodide-Mediated or Iodide-Catalyzed Demethylation and Friedel-Crafts C-H Borylative Cyclization Leading to Thiophene-Fused 1,2-Oxaborine Derivatives
Shigemori, Keisuke
Watanabe, Momoka
Kong, Julie
Mitsudo, Koichi
Wakamiya, Atsushi
Mandai, Hiroki
Suga, Seiji
ORGANIC LETTERS, 2019, 21 (07) : 2171 - 2175
[37] Organocatalytic Asymmetric Synthesis of Aza-Spirooxindoles via Michael/Friedel-Crafts Cascade Reaction of 1,3-Nitroenynes and 3-Pyrrolyloxindoles
Ni, Qijian
Wang, Xuyang
Zeng, Da
Wu, Qianling
Song, Xiaoxiao
ORGANIC LETTERS, 2021, 23 (06) : 2273 - 2278
[38] Synthesis of difluoromethylated diarylmethanes via Fe(OTf)3-catalyzed Friedel-Crafts reaction of 2,2-difluoro-1-arylethyl phosphates
Yamamoto, Yoshihiko
Takase, Tomoya
Kuroyanagi, Eisuke
Yasui, Takeshi
CHEMICAL COMMUNICATIONS, 2021, 57 (32) : 3877 - 3880
[39] REACTIONS OF SOME SUBSTITUTED 1,2,4-TRIAZINES WITH BENZENE UNDER FRIEDEL-CRAFTS CONDITIONS .1. SYNTHESIS OF SOME NEW 5-SUBSTITUTED 6-AZAURACIL DERIVATIVES
IBRAHIM, YA
EID, MM
INDIAN JOURNAL OF CHEMISTRY, 1975, 13 (10): : 1098 - 1100
[40] Chiral NCN Pincer Pt(II) and Pd(II) Complexes with 1,3-Bis(2′-imidazolinyl)benzene: Synthesis via Direct Metalation, Characterization, and Catalytic Activity in the Friedel-Crafts Alkylation Reaction
Wu, Li-Yuan
Hao, Xin-Qi
Xu, Yan-Xiao
Jia, Min-Qiang
Wang, Ya-Nan
Gong, Jun-Fang
Song, Mao-Ping
ORGANOMETALLICS, 2009, 28 (12) : 3369 - 3380

← 1 2 3 4 5 →