Rh(III)-Catalyzed Oxidative Olefination of N-(1-Naphthyl)sulfonamides Using Activated and Unactivated Alkenes

被引：96

作者：

Li, Xuting ^{[1
,2
]}

Gong, Xue ^{[1
]}

Zhao, Miao ^{[1
]}

Song, Guoyong ^{[1
]}

Deng, Jian ^{[2
]}

Li, Xingwei ^{[1
]}

机构：

[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China

[2] Univ S China, Sch Chem & Chem Engn, Hengyang 421001, Peoples R China

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 21期

关键词：

CATALYZED ORTHO-OLEFINATION; H BOND-CLEAVAGE; ARYL IODIDES; ALKYNES; DERIVATIVES; ARENES; ACIDS; N; N-DIMETHYLFORMAMIDE; FUNCTIONALIZATION; ALKYLATION;

D O I：

10.1021/ol2023856

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rhodium(III)-catalyzed oxidative olefination of N-(1-naphthyl)sulfonamides has been achieved at the peri position. Three categories of olefins have been successfully applied. Activated olefins reacted to afford five-membered azacycles as a result of oxidative olefination-hydroamination. Unactivated olefins reacted to give the olefination product. 2-fold oxidative C-C and C-N coupling was achieved for allylbenzenes.

引用

页码：5808 / 5811

页数：4

共 45 条

[21] Rhodium(III)-Catalyzed Oxidative ortho-Olefination of Phenyl Carbamates with Alkenes: Elucidation of Acceleration Mechanisms by Using an Unsubstituted Cyclopentadienyl Ligand
Tanaka, Jin
Nagashima, Yuki
Tanaka, Ken
ORGANIC LETTERS, 2020, 22 (18) : 7181 - 7186
[22] Mechanism of Rh(III)-catalyzed cyclopropanation using N-enoxyphthalimides and alkenes: Insights from DFT calculations
Deng, Jiaojiao
Wen, Xiuling
Qiu, Zhiping
Li, Juan
TETRAHEDRON, 2016, 72 (51) : 8456 - 8462
[23] SPECTROPHOTOMETRIC DETERMINATION OF ACADESINE (AICA-RIBOSIDE) IN PLASMA USING A DIAZOTIZATION COUPLING TECHNIQUE WITH N-(1-NAPHTHYL)ETHYLENEDIAMINE
FUJITAKI, JM
SANDOVAL, TM
LEMBACH, LA
DIXON, R
JOURNAL OF BIOCHEMICAL AND BIOPHYSICAL METHODS, 1994, 29 (02): : 143 - 148
[24] Flow-injection catalytic spectrophotometic determination of molybdenum(VI) in plants using bromate oxidative coupling of p-hydrazinobensenesulfonic acid with N-(1-naphthyl)ethylenediamine
Nakano, Shigenori
Kamaguchi, Chie
Hirakawa, Naoki
TALANTA, 2010, 81 (03) : 786 - 791
[25] Development of a Selective and Sensitive Spectrophotometric Method for the Trace Determination of Thallium(III) Using 3-Methyl-2-benzothiazolinone Hydrazone Hydrochloride and N-(1-naphthyl)-ethylenediamine Dihydrochloride
Nagaraja, Padmarajaiah
Al-Tayar, Naef Ghllab Saeed
Kumar, Anantharaman Shiva
JOURNAL OF AOAC INTERNATIONAL, 2008, 91 (05) : 1116 - 1123
[26] Development of a selective and sensitive spectrophotometric method for the trace determination of thallium(III) using 3-methyl-2-benzothiazolinone hydrazone hydrochloride and N-(1-naphthyl)-ethylenediamine dihydrochloride
Nagaraja, Padmarajaiah
Al-Tayar, Naef Ghllab Saeed
Kumar, Anantharaman Shiva
Journal of AOAC International, 1600, 91 (05): : 1116 - 1123
[27] [2+2+2] Annulation of N-(1-Naphthyl)acetamide with Two Alkynoates via Cleavage of Adjacent C-H and C-N Bonds Catalyzed by an Electron-Deficient Rhodium(III) Complex
Terasawa, Jyunichi
Shibata, Yu
Fukui, Miho
Tanaka, Ken
MOLECULES, 2018, 23 (12):
[28] Determination of peimine and peiminine in Bulbus Fritillariae Thunbergii by capillary electrophoresis by indirect UV detection using N-(1-naphthyl)ethylenediamine dihydrochloride as probe
Liu, Lihong
You, Wenwei
Zheng, Liujuan
Chen, Feiyu
Jia, Zhimin
ELECTROPHORESIS, 2012, 33 (14) : 2152 - 2158
[29] Selective electrochemical detection of ascorbic acid in canned juice using aniline/N-(1-naphthyl)ethylene-diamine modified MWCNT electrode
Vishnu, Nandimalla
Kumar, Annamalai Senthil
JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2015, 92 (04) : 489 - 492
[30] Aqua[N-(1-naphthyl)acetamido-κN]bis-[2-(2-pyridyl)phenyl-κ2 N,C1] iridium(III) ethylene glycol hemisolvate
Fu, Hao
Ding, Yuqiang
Chen, Guoqing
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : M731 - U1017

← 1 2 3 4 5 →