One-pot borylation/amination reactions: Syntheses of arylamine boronate esters from halogenated arenes

被引：43

作者：

Holmes, D ^{[1
]}

Chotana, GA ^{[1
]}

Maleczka, RE ^{[1
]}

Smith, MR ^{[1
]}

机构：

[1] Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 07期

关键词：

D O I：

10.1021/ol060205y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot protocol for converting 1,3- and 1,4-substituted aryl halides to arylamine boronate esters is described. This is achieved by sequential Ir-catalyzed aromatic borylation at the least hindered C-H bond of the aryl halide and subsequent Pd-catalyzed CA coupling at the halide position of the crude arylboronic ester.

引用

页码：1407 / 1410

页数：4

共 24 条

[1] Assessing the benefits of direct isolation processes [J].

Anderson, NG .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2004, 8 (02) :260-265

[2] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].

Barder, TE ;

Walker, SD ;

Martinelli, JR ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696

[3] Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds [J].

Cho, JY ;

Tse, MK ;

Holmes, D ;

Maleczka, RE ;

Smith, MR .

SCIENCE, 2002, 295 (5553) :305-308

[4]

CHOTANA AG, UNPUB

[5] Synthesis, SAR, and antitumor properties of diamino-C,N-diarylpyrimidine positional isomers:: inhibitors of lysophosphatidic acid acyltransferase-β [J].

Gong, BQ ;

Hong, F ;

Kohm, C ;

Jenkins, S ;

Tulinsky, J ;

Bhatt, R ;

de Vries, P ;

Singer, JW ;

Klein, P .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (09) :2303-2308

[6] Carbon-heteroatom bond-forming reductive eliminations of amines, ethers, and sulfides [J].

Hartwig, JF .

ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (12) :852-860

[7] Synthesis of para-substituted 3-formyl arylboronic esters [J].

Holland, R ;

Spencer, J ;

Deadman, JJ .

SYNTHESIS-STUTTGART, 2002, (16) :2379-2382

[8] Room temperature borylation of arenes and heteroarenes using stoichiometric amounts of pinacolborane catalyzed by iridium complexes in an inert solvent [J].

Ishiyama, T ;

Nobuta, Y ;

Hartwig, JF ;

Miyaura, N .

CHEMICAL COMMUNICATIONS, 2003, (23) :2924-2925

[9] Iridium-catalyzed direct borylation of five-membered heteroarenes by bis(pinacolato)diboron: Regioselective, stoichiometric, and room temperature reactions [J].

Ishiyama, T ;

Takagi, J ;

Yonekawa, Y ;

Hartwig, JF ;

Miyaura, N .

ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (9-10) :1103-1106

[10] Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate [J].

Ishiyama, T ;

Takagi, J ;

Ishida, K ;

Miyaura, N ;

Anastasi, NR ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (03) :390-391

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