C-H functionalization of tetramethylsilane employing a borylnitrene

被引：14

作者：

Mueller, Matthias ^{[1
]}

Maichle-Moessmer, Caecilia ^{[2
]}

Bettinger, Holger F. ^{[1
]}

机构：

[1] Univ Tubingen, Inst Organ Chem, D-72076 Tubingen, Germany

[2] Univ Tubingen, Inst Anorgan Chem, D-72076 Tubingen, Germany

来源：

CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 100期

关键词：

CARBON-HYDROGEN-BONDS; INTERMOLECULAR ACTIVATION; METHANE; COMPLEXES; INSERTION; INSIGHTS;

D O I：

10.1039/c3cc47753c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The irradiation of 2-azido-4,4,5,5-tetramethyl-1,3,2-dioxaborol (pinBN(3), pin = pinacolato) generates the corresponding borylnitrene that easily inserts into the CH bond of tetramethylsilane. This primary photo-product, a monoborylated aminoborane, undergoes a subsequent reaction with pinBN3 forming a bisborylated aminoborane.

引用

页码：11773 / 11775

页数：3

共 41 条

[1] Thermal activation of hydrocarbon C-H bonds by tungsten alkylidene complexes [J].

Adams, CS ;

Legzdins, P ;

Tran, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (04) :612-624

[2] Mechanistic Insights into C-H Amination via Dicopper Nitrenes [J].

Aguila, Mae Joanne B. ;

Badiei, Yosra M. ;

Warren, Timothy H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (25) :9399-9406

[3] REACTIONS OF CARBOALKOXYCARBENES WITH ALKYLSILANES [J].

ANDO, W ;

KONISHI, K ;

MIGITA, T .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 67 (01) :C7-C9

[4] SELECTIVE INTERMOLECULAR CARBON-HYDROGEN BOND ACTIVATION BY SYNTHETIC METAL-COMPLEXES IN HOMOGENEOUS SOLUTION [J].

ARNDTSEN, BA ;

BERGMAN, RG ;

MOBLEY, TA ;

PETERSON, TH .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (03) :154-162

[5] EFFECTS OF GROUP IVA ORGANOMETALLICS ON REACTION OF ETHOXYCARBONYLNITRENE WITH CYCLOHEXENE [J].

BELLOLI, R ;

WOLLENBE.RH ;

JAEGER, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (11) :1857-&

[6] Metal-free conversion of methane and cycloalkanes to amines and amides by employing a borylnitrene [J].

Bettinger, Holger F. ;

Filthaus, Matthias ;

Bornemann, Holger ;

Oppel, Iris M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (25) :4744-4747

[7] Donor stabilized borylnitrene: A highly reactive BN analogue of vinylidene [J].

Bettinger, Holger F. ;

Bornemann, Holger .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (34) :11128-11134

[8] Borylnitrenes: electrophilic reactive intermediates with high reactivity towards C-H bonds [J].

Bettinger, Holger F. ;

Filthaus, Matthias .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (24) :5477-5482

[9] Insertion into dihydrogen employing the nitrogen centre of a borylnitrene [J].

Bettinger, Holger F. ;

Filthaus, Matthias ;

Neuhaus, Patrik .

CHEMICAL COMMUNICATIONS, 2009, (16) :2186-2188

[10] Studies in catalytic C-H amination involving nitrene C-H insertion [J].

Collet, Florence ;

Lescot, Camille ;

Liang, Chungen ;

Dauban, Philippe .

DALTON TRANSACTIONS, 2010, 39 (43) :10401-10413

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