Chemo- and regioselective remote functionalization of nonanamides via sp3 C-H bond cleavage under superelectrophilic conditions

被引：5

作者：

Akhrem, Irena S. ^{[1
]}

Afanas'eva, Lyudmila V. ^{[1
]}

Churilova, Irina M. ^{[1
]}

Artyushin, Oleg I. ^{[1
]}

Kagramanov, Nikolai D. ^{[1
]}

机构：

[1] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Moscow 119991, Russia

来源：

MENDELEEV COMMUNICATIONS | 2015年 / 25卷 / 02期

基金：

俄罗斯基础研究基金会;

关键词：

ONE-POT SYNTHESIS; SELECTIVE CARBONYLATION; CARBON-MONOXIDE; ORTHO-ARYLATION; ACIDS; ALKANE; SUPERACIDS; ALCOHOLS; KETONES;

D O I：

10.1016/j.mencom.2015.03.015

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Treatment of nonanamides C8H17C(O)NR2 (R = H or Et) with superelectrophilic complex CBr4 center dot 2AlBr(3) under CO atmosphere followed by quenching with nucleophiles NuH cleanly gives 7-methyl-7-(Nu-carbonyl)octanamide bifunctional derivatives.

引用

页码：124 / 125

页数：2

共 35 条

[1] A NOVEL FAMILY OF APROTIC ORGANIC SUPERACIDS FOR LOW-TEMPERATURE ALKANE AND CYCLOALKANE TRANSFORMATIONS [J].

AKHREM, I ;

ORLINKOV, A ;

VOLPIN, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (08) :671-672

[2] Polyhalomethanes combined with lewis acids in alkane chemistry [J].

Akhrem, Irena ;

Orlinkov, Alexander .

CHEMICAL REVIEWS, 2007, 107 (05) :2037-2079

[3] The first one-pot 'alkane-like' reactions of carbonyl-containing adamantanes [J].

Akhrem, Irena ;

Avetisyan, Dzhul'etta ;

Afanas'eva, Lyudmila ;

Kagramanov, Nikolai ;

Petrovskii, Pavel ;

Orlinkov, Alexander .

TETRAHEDRON LETTERS, 2010, 51 (06) :907-911

[4] Intermolecular sp3 C-H bond functionalization of alkyl alkanoates as a new method for the one-pot synthesis of functional neo alkyl alkanoates with remote functional groups [J].

Akhrem, Irena S. ;

Avetisyan, Dzhul'etta V. ;

Churilova, Irina M. ;

Afanas'eva, Lyudmila V. ;

Artyushin, Oleg I. ;

Kagramanov, Nikolai D. .

TETRAHEDRON LETTERS, 2013, 54 (45) :6037-6040

[5] The first selective one-pot synthesis of 1,3-dicarbonyl adamantanes from adamantane and 1,3-dimethyladamantane [J].

Akhrem, Irena S. ;

Avetisyan, Dzhul'etta V. ;

Afanas'eva, Luidmila V. .

TETRAHEDRON LETTERS, 2012, 53 (27) :3493-3496

[6] Superelectrophilic sp3 C-H carbonylation of n-octyl acetate as a way to new bifunctional neo-octanes [J].

Akhrem, Irena S. ;

Avetisyan, Dzhul'etta V. ;

Afanas'eva, Lyudmila V. ;

Orlinkov, Alexander V. ;

Kagramanov, Nikolai D. ;

Petrovskii, Pavel V. .

MENDELEEV COMMUNICATIONS, 2011, 21 (06) :323-325

[7] The first one-pot synthesis of 1,3-dicarbonyl adamantanes from 1-bromoadamantanes [J].

Akhrem, Irena S. ;

Avetisyan, Dzhul'etta V. ;

Afanas'eva, Lyudmila V. ;

Goryunov, Evgenii I. ;

Churilova, Irina M. ;

Petrovskii, Pavel V. ;

Kagramanov, Nikolai D. .

MENDELEEV COMMUNICATIONS, 2011, 21 (05) :259-261

[8] First examples of the selective carbonylation of C6-C10 linear alkanes to tertiary carbonyl-containing compounds [J].

Akhrem, IS ;

Afanas'eva, LV ;

Vitt, SV ;

Petrovskii, PV .

MENDELEEV COMMUNICATIONS, 2002, (05) :180-182

[9]

Akluvm I. S., 2012, TETRAHEDRON LETT, V53, P4221

[10]

[Anonymous], ACS S SERIES

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