Oxidative C-N Bond Formation of Isochromans Using an Electronically Tuned Nitroxyl Radical as Catalyst

被引:0
作者
Yano, Kyoko [1 ]
Ohshimo, Ayano [1 ]
Elboray, Elghareeb E. [1 ,2 ]
Kobayashi, Yusuke [1 ]
Furuta, Takumi [1 ]
Hamada, Shohei [1 ]
机构
[1] Kyoto Pharmaceut Univ, Lab Pharmaceut Chem, Yamashinaku, Kyoto 6078412, Japan
[2] South Valley Univ, Fac Sci, Dept Chem, Qena 83523, Egypt
来源
SYNOPEN | 2024年 / 08卷 / 02期
关键词
isochroman; cross-dehydrogenative coupling; nitroxyl radical; C-N bond formation; organocatalyst; oxidation; H BONDS; CHEMOSELECTIVE OXIDATION; AEROBIC OXIDATION; ETHERS; ALCOHOLS; TEMPO; MILD;
D O I
10.1055/s-0040-1720118
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The cross-dehydrogenative coupling between isochromansand nucleophiles using an electronically tuned nitroxyl radical catalyst,which effectively promotes the oxidation of benzylic ethers, has beeninvestigated. Using sulfonamides as a nucleophile, modification of isochromans via oxidative C-N bond formation has been achieved at ambient temperature.
引用
收藏
页码:125 / 129
页数:5
相关论文
共 34 条
[1]   Mechanism of the oxidation of alcohols by oxoammonium cations [J].
Bailey, William F. ;
Bobbitt, James M. ;
Wiberg, Kenneth B. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (12) :4504-4509
[2]   Benzylic oxidation catalyzed by dirhodium(II,III) caprolactamate [J].
Catino, AJ ;
Nichols, JM ;
Choi, H ;
Gottipamula, S ;
Doyle, MP .
ORGANIC LETTERS, 2005, 7 (23) :5167-5170
[3]   Industrial Oxidations with Organocatalyst TEMPO and Its Derivatives [J].
Ciriminna, Rosaria ;
Pagliaro, Mario .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2010, 14 (01) :245-251
[4]   A very mild and chemoselective oxidation of alcohols to carbonyl compounds [J].
De Luca, L ;
Giacomelli, G ;
Porcheddu, A .
ORGANIC LETTERS, 2001, 3 (19) :3041-3043
[5]   A versatile and highly selective hypervalent iodine (III)/2,2,6,6-tetramethyl-1-piperidinyloxyl-mediated oxidation of alcohols to carbonyl compounds [J].
DeMico, A ;
Margarita, R ;
Parlanti, L ;
Vescovi, A ;
Piancatelli, G .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) :6974-6977
[6]  
deNooy AEJ, 1996, SYNTHESIS-STUTTGART, P1153
[7]   Dehydrogenative α-Oxygenation of Ethers with an Iron Catalyst [J].
Gonzalez-de-Castro, Angela ;
Robertson, Craig M. ;
Xiao, Jianliang .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (23) :8350-8360
[8]   METABOLIC PRODUCTS OF FUSARIUM-LARVARUM FUCKEL - FUSARENTINS AND THE ABSOLUTE-CONFIGURATION OF MONOCERIN [J].
GROVE, JF ;
POPLE, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (08) :2048-2051
[9]   Oxidative Deprotection of Benzyl Protecting Groups for Alcohols by an Electronically Tuned Nitroxyl-Radical Catalyst [J].
Hamada, Shohei ;
Sumida, Maiko ;
Yamazaki, Rikako ;
Kobayashi, Yusuke ;
Furuta, Takumi .
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (17) :12464-12473
[10]   Diverse Site-Selective Transformation of Benzylic and Allylic Silyl Ethers via Organocatalytic Oxidation [J].
Hamada, Shohei ;
Sakamoto, Kaori ;
Miyazaki, Eri ;
Elboray, Elghareeb E. ;
Kobayashi, Yusuke ;
Furuta, Takumi .
ACS CATALYSIS, 2023, 13 (12) :8031-8037