Copper-Catalyzed Oxidative -Alkylation of -Amino Carbonyl Compounds with Ethers via Dual C(sp3)-H Oxidative Cross- Coupling

被引:121
作者
Wei, Wen-Ting [1 ]
Song, Ren-Jie [1 ]
Li, Jin-Heng [1 ]
机构
[1] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemo Biosensing & Chemometr, Changsha 410082, Hunan, Peoples R China
关键词
alkylation; -amino carbonyl compounds; tert-butyl hydrogen peroxide (TBHP); copper; C(sp3)H functionalization; ethers; C-H BONDS; NATURAL-PRODUCTS; PHOTOINDUCED FORMATION; ASYMMETRIC-SYNTHESIS; DIRECT ARYLATION; ALPHA-ARYLATION; DERIVATIVES; VINYL; ALKENYLATION; CHEMISTRY;
D O I
10.1002/adsc.201301091
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A novel copper-catalyzed oxidative alkylation of -amino carbonyl compounds with ethers has been established for the selective synthesis of -etherized -amino carbonyl compounds. This oxidative alkylation is achieved by dual C(sp3)H bond oxidative cross-coupling, and its scope is expanded to -amino ketones, -amino esters and -amino amides.
引用
收藏
页码:1703 / 1707
页数:5
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共 69 条
[21]   Foldamers: A manifesto [J].
Gellman, SH .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (04) :173-180
[22]   Alkynylation of C-H bonds via reaction with acetylenic triflones [J].
Gong, JC ;
Fuchs, PL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (18) :4486-4487
[23]   Recent development and application of chiral phase-transfer catalysts [J].
Hashimoto, Takuya ;
Maruoka, Keiji .
CHEMICAL REVIEWS, 2007, 107 (12) :5656-5682
[24]   PHOTOINDUCED FORMATION AND REACTION OF BENZALANILINE RADICAL-ANIONS - COMPARISON WITH THE RADIATION-INDUCED REACTION [J].
ISHIDA, A ;
SUGITA, D ;
TAKAMUKU, S .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1992, 65 (1-2) :197-204
[25]   SITE-SPECIFIC SUBSTITUENT EFFECT ON THE PHOTOINDUCED FORMATION OF BENZALANILINE RADICAL-ANION IN 2-METHYLTETRAHYDROFURAN AT 77 K [J].
ISHIDA, A ;
SUGITA, D ;
ITOH, Y ;
TAKAMUKU, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (47) :11687-11694
[26]   Synthetic strategies of marine polycyclic ethers via intramolecular allylations: Linear and convergent approaches [J].
Kadota, I ;
Yamamoto, Y .
ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (05) :423-432
[27]   Total synthesis of oxacyclic macrodiolide natural products [J].
Kang, EJ ;
Lee, E .
CHEMICAL REVIEWS, 2005, 105 (12) :4348-4378
[28]   Cu2O Nanocubes Catalyzed Difunctionalization Reaction of Vinyl Arenes with Cyclic Ethers [J].
Kim, Jee Young ;
Park, Ji Chan ;
Song, Hyunjoon ;
Park, Kang Hyun .
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2010, 31 (12) :3509-3510
[29]   Asymmetric hydrogenation of prochiral amino ketones to amino alcohols for pharmaceutical use [J].
Klingler, Franz Dietrich .
ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (12) :1367-1376
[30]   Catalytic Oxidative Coupling Reactions for the Formation of Carbon-Carbon Bonds without Carbon-Metal Intermediates [J].
Klussmann, Martin ;
Sureshkumar, Devarajulu .
SYNTHESIS-STUTTGART, 2011, (03) :353-369