Thieme Chemistry Journal Awardees - Where Are They Now? Palladium-Catalyzed N-Arylation-Hydroamination Sequence for the Synthesis of Indoles with Sterically Demanding N-Substituents

被引：36

作者：

Ackermann, Lutz ^{[1
]}

Sandmann, Rene ^{[1
]}

Kondrashov, Mikhail V. ^{[1
]}

机构：

[1] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany

来源：

SYNLETT | 2009年 / 08期

关键词：

amination; heteroarenes; hydroamination; indoles; palladium; ANNULATION; FUNCTIONALIZATION; CASCADE; ALKYNES; AIR;

D O I：

10.1055/s-0029-1216727

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium-catalyzed sequence consisting of an N-arylation and ail intramolecular hydroamination sets the stage for a modular synthesis of indoles bearing sterically hindered N-substituents.

引用

页码：1219 / 1222

页数：4

共 43 条

[1] General and efficient indole syntheses based on catalytic amination reactions [J].

Ackermann, L .

ORGANIC LETTERS, 2005, 7 (03) :439-442

[2] TiCl4/t-BuNH2 as the sole catalyst for a hydroamination-based Fischer indole synthesis [J].

Ackermann, L ;

Born, R .

TETRAHEDRON LETTERS, 2004, 45 (52) :9541-9544

[3] Hydroamination/Heck reaction sequence for a highly regioselective one-pot synthesis of indoles using 2-chloroaniline [J].

Ackermann, L ;

Kaspar, LT ;

Gschrei, CJ .

CHEMICAL COMMUNICATIONS, 2004, (24) :2824-2825

[4] Annulation of internal alkynes through a hydroamination/aza-Heck reaction sequence for the regioselective synthesis of indoles [J].

Ackermann, Lutz ;

Sandmann, Rene ;

Villar, Amparo ;

Kaspar, Ludwig T. .

TETRAHEDRON, 2008, 64 (05) :769-777

[5] One-pot 2-aryl/vinylindole synthesis consisting of a ruthenium-catalyzed hydroamination and a palladium-catalyzed Heck reaction using 2-chloroaniline [J].

Ackermann, Lutz ;

Althammer, Andreas .

SYNLETT, 2006, (18) :3125-3129

[6] Catalytic arylations with challenging substrates: From air-stable HASPO preligands to indole syntheses and C-H-bond functionalizations [J].

Ackermann, Lutz .

SYNLETT, 2007, (04) :507-526

[7] Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].

Alonso, F ;

Beletskaya, IP ;

Yus, M .

CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159

[8] METABOLIC PRODUCTS OF ASPERGILLUS-TERREUS .10. BIOSYNTHESIS OF ASTERRIQUINONES [J].

ARAI, K ;

YAMAMOTO, Y .

CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (11) :2929-2932

[9] Direct palladium-catalyzed C-3 arylation of free (NH)-indoles with aryl bromides under ligandless conditions [J].

Bellina, Fabio ;

Benelli, Francesca ;

Rossi, Renzo .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14) :5529-5535

[10] Silver-Promoted Domino Pd-Catalyzed Amination/Direct Arylation: Access to Polycyclic Heteroaromatics [J].

Bryan, Christopher S. ;

Lautens, Mark .

ORGANIC LETTERS, 2008, 10 (20) :4633-4636

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