Radical reduction of aromatic azides to amines with triethylsilane

被引：58

作者：

Benati, Luisa ^{[1
]}

Bencivenni, Giorgio ^{[1
]}

Leardini, Rino ^{[1
]}

Minozzi, Matteo ^{[1
]}

Nanni, Daniele ^{[1
]}

Scialpi, Rosanna ^{[1
]}

Spagnolo, Piero ^{[1
]}

Zanardi, Giuseppe ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 15期

关键词：

D O I：

10.1021/jo060824k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aromatic azides are inert toward triethylsilane under thermal conditions in the presence of a radical initiator, but in the presence of additional catalytic amounts of tert-do-decanethiol, they afford anilinosilanes and thence the corresponding anilines in virtually quantitative yields.

引用

页码：5822 / 5825

页数：4

共 51 条

[1] Selected methods for the reduction of the azido group [J].

Amantini, D ;

Fringuelli, F ;

Pizzo, F ;

Vaccaro, L .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2002, 34 (02) :109-+

[2] Efficient one-pot synthesis of 1-aryl 1,2,3-triazoles from aryl halides and terminal alkynes in the presence of sodium azide [J].

Andersen, J ;

Bolvig, S ;

Liang, XF .

SYNLETT, 2005, (19) :2941-2947

[3] Rapid synthesis of aryl azides from aryl halides under mild conditions [J].

Andersen, J ;

Madsen, U ;

Björkling, F ;

Liang, XF .

SYNLETT, 2005, (14) :2209-2213

[4]

ANDO W, 1982, SYNTHESIS-STUTTGART, P263

[5] Radical reduction of aromatic azides to amines with tributylgermanium hydride [J].

Benati, L ;

Bencivenni, G ;

Leardini, R ;

Minozzi, M ;

Nanni, D ;

Scialpi, R ;

Spagnolo, P ;

Zanardi, G .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) :434-437

[6] Thermal reactions of tributyltin hydride with α-azido esters:: Unexpected intervention of tin triazene adducts under both nonradical and radical conditions [J].

Benati, L ;

Bencivenni, G ;

Leardini, R ;

Minozzi, M ;

Nanni, D ;

Scialpi, R ;

Spagnolo, P ;

Zanardi, G .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) :3046-3053

[7] Cyclizations of N-stannylaminyl radicals onto nitriles [J].

Benati, L ;

Bencivenni, G ;

Leardini, R ;

Minozzi, M ;

Nanni, D ;

Scialpi, R ;

Spagnolo, P ;

Zanardi, G ;

Rizzoli, C .

ORGANIC LETTERS, 2004, 6 (03) :417-420

[8] Radical chain reactions of α-azido ketones with tributyltin hydride:: reduction vs nitrogen insertion and 1,2-hydrogen shift in the intermediate N-stannylaminyl radicals [J].

Benati, L ;

Leardini, R ;

Minozzi, M ;

Nanni, D ;

Spagnolo, P ;

Strazzari, S ;

Zanardi, G ;

Calestani, G .

TETRAHEDRON, 2002, 58 (18) :3485-3492

[9]

BENATI L, 1978, TETRAHEDRON LETT, P815

[10] REACTIVITY OF AN (ARYLTHIO) THIOCARBONYL RADICAL - INTRAMOLECULAR ADDITION TO THE AZIDO GROUP [J].

BENATI, L ;

MONTEVECCHI, PC .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (22) :4570-4573

← 1 2 3 4 5 6 →