Pd- and Cu-catalyzed C-H arylation of indazoles

Keika Hattori; Kazuya Yamaguchi; Junichiro Yamaguchi; Kenichiro Itami

doi:10.1016/j.tet.2012.05.091

Pd- and Cu-catalyzed C-H arylation of indazoles

Keika Hattori, Kazuya Yamaguchi, Junichiro Yamaguchi, Kenichiro Itami^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

73 Citations (Scopus)

Abstract

The palladium- and copper-catalyzed C-H arylation reactions of 1H- and 2H-indazoles with haloarenes are described. A PdCl ₂/phen/Ag ₂CO ₃/K ₃PO ₄ catalytic system is effective for the C-H arylation of 1H- and 2H-indazoles with haloarenes, whereas a less expensive CuI/phen/LiOt-Bu catalytic system is applicable to the C-H coupling of substituted 2H-indazoles and iodoarenes. The utility of newly developed catalyst was demonstrated in the rapid synthesis of YC-1 (an antitumor agent) and YD-3 (platelet anti-aggregating agent). These new reactions represent important direct functionalization tools of indazoles, well-known bioisosteres of pharmaceutically important indole core.

Original language	English
Pages (from-to)	7605-7612
Number of pages	8
Journal	Tetrahedron
Volume	68
Issue number	37
DOIs	https://doi.org/10.1016/j.tet.2012.05.091
Publication status	Published - 2012 Sept 16
Externally published	Yes

Keywords

C-H arylation
Catalysis
Heterobiaryl
Indazole

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2012.05.091

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title = "Pd- and Cu-catalyzed C-H arylation of indazoles",

abstract = "The palladium- and copper-catalyzed C-H arylation reactions of 1H- and 2H-indazoles with haloarenes are described. A PdCl 2/phen/Ag 2CO 3/K 3PO 4 catalytic system is effective for the C-H arylation of 1H- and 2H-indazoles with haloarenes, whereas a less expensive CuI/phen/LiOt-Bu catalytic system is applicable to the C-H coupling of substituted 2H-indazoles and iodoarenes. The utility of newly developed catalyst was demonstrated in the rapid synthesis of YC-1 (an antitumor agent) and YD-3 (platelet anti-aggregating agent). These new reactions represent important direct functionalization tools of indazoles, well-known bioisosteres of pharmaceutically important indole core.",

keywords = "C-H arylation, Catalysis, Heterobiaryl, Indazole",

author = "Keika Hattori and Kazuya Yamaguchi and Junichiro Yamaguchi and Kenichiro Itami",

note = "Funding Information: This work was supported by the Funding Program for Next Generation World-Leading Researchers from JSPS ( 220GR049 to K.I.) and the Grant-in-Aid for Scientific Research on Innovative Areas {\textquoteleft}Molecular Activation Directed toward Straightforward Synthesis{\textquoteright} ( 23105517 to J.Y.) from MEXT . ",

year = "2012",

month = sep,

day = "16",

doi = "10.1016/j.tet.2012.05.091",

language = "English",

volume = "68",

pages = "7605--7612",

journal = "Tetrahedron",

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T1 - Pd- and Cu-catalyzed C-H arylation of indazoles

AU - Hattori, Keika

AU - Yamaguchi, Kazuya

AU - Yamaguchi, Junichiro

AU - Itami, Kenichiro

N1 - Funding Information: This work was supported by the Funding Program for Next Generation World-Leading Researchers from JSPS ( 220GR049 to K.I.) and the Grant-in-Aid for Scientific Research on Innovative Areas ‘Molecular Activation Directed toward Straightforward Synthesis’ ( 23105517 to J.Y.) from MEXT .

PY - 2012/9/16

Y1 - 2012/9/16

N2 - The palladium- and copper-catalyzed C-H arylation reactions of 1H- and 2H-indazoles with haloarenes are described. A PdCl 2/phen/Ag 2CO 3/K 3PO 4 catalytic system is effective for the C-H arylation of 1H- and 2H-indazoles with haloarenes, whereas a less expensive CuI/phen/LiOt-Bu catalytic system is applicable to the C-H coupling of substituted 2H-indazoles and iodoarenes. The utility of newly developed catalyst was demonstrated in the rapid synthesis of YC-1 (an antitumor agent) and YD-3 (platelet anti-aggregating agent). These new reactions represent important direct functionalization tools of indazoles, well-known bioisosteres of pharmaceutically important indole core.

AB - The palladium- and copper-catalyzed C-H arylation reactions of 1H- and 2H-indazoles with haloarenes are described. A PdCl 2/phen/Ag 2CO 3/K 3PO 4 catalytic system is effective for the C-H arylation of 1H- and 2H-indazoles with haloarenes, whereas a less expensive CuI/phen/LiOt-Bu catalytic system is applicable to the C-H coupling of substituted 2H-indazoles and iodoarenes. The utility of newly developed catalyst was demonstrated in the rapid synthesis of YC-1 (an antitumor agent) and YD-3 (platelet anti-aggregating agent). These new reactions represent important direct functionalization tools of indazoles, well-known bioisosteres of pharmaceutically important indole core.

KW - C-H arylation

KW - Catalysis

KW - Heterobiaryl

KW - Indazole

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U2 - 10.1016/j.tet.2012.05.091

DO - 10.1016/j.tet.2012.05.091

M3 - Article

AN - SCOPUS:84864445459

SN - 0040-4020

VL - 68

SP - 7605

EP - 7612

JO - Tetrahedron

JF - Tetrahedron

IS - 37

ER -

Pd- and Cu-catalyzed C-H arylation of indazoles

Abstract

Keywords

ASJC Scopus subject areas

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