Iridium-catalyzed selective synthesis of 4-substituted benzofurans and indoles via directed cyclodehydration

Kyoji Tsuchikama; Yu Ki Hashimoto; Kohei Endo; Takanori Shibata

doi:10.1002/adsc.200900570

Iridium-catalyzed selective synthesis of 4-substituted benzofurans and indoles via directed cyclodehydration

Kyoji Tsuchikama, Yu Ki Hashimoto, Kohei Endo, Takanori Shibata^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

88 Citations (Scopus)

Abstract

A directed cyclization-dehydration cascade of α-aryloxy ketones and α-arylamino ketones was efficiently catalyzed by a cationic iridiumBINAP complex, which afforded various types of 4-substituted benzofurans and indoles in high yields with complete regioselectivity. The newly developed protocol also enabled the enantioselective preparation of chiral 4-acetyloxindole using a chiral iridium catalyst.

Original language	English
Pages (from-to)	2850-2854
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	351
Issue number	17
DOIs	https://doi.org/10.1002/adsc.200900570
Publication status	Published - 2009 Nov 1

Keywords

C-C bond formation
C-H functionalization
Heterocycles
Homogeneous catalysis
Iridium

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.200900570

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title = "Iridium-catalyzed selective synthesis of 4-substituted benzofurans and indoles via directed cyclodehydration",

abstract = "A directed cyclization-dehydration cascade of α-aryloxy ketones and α-arylamino ketones was efficiently catalyzed by a cationic iridiumBINAP complex, which afforded various types of 4-substituted benzofurans and indoles in high yields with complete regioselectivity. The newly developed protocol also enabled the enantioselective preparation of chiral 4-acetyloxindole using a chiral iridium catalyst.",

keywords = "C-C bond formation, C-H functionalization, Heterocycles, Homogeneous catalysis, Iridium",

author = "Kyoji Tsuchikama and Hashimoto, {Yu Ki} and Kohei Endo and Takanori Shibata",

year = "2009",

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AU - Tsuchikama, Kyoji

AU - Hashimoto, Yu Ki

AU - Endo, Kohei

AU - Shibata, Takanori

PY - 2009/11/1

Y1 - 2009/11/1

N2 - A directed cyclization-dehydration cascade of α-aryloxy ketones and α-arylamino ketones was efficiently catalyzed by a cationic iridiumBINAP complex, which afforded various types of 4-substituted benzofurans and indoles in high yields with complete regioselectivity. The newly developed protocol also enabled the enantioselective preparation of chiral 4-acetyloxindole using a chiral iridium catalyst.

AB - A directed cyclization-dehydration cascade of α-aryloxy ketones and α-arylamino ketones was efficiently catalyzed by a cationic iridiumBINAP complex, which afforded various types of 4-substituted benzofurans and indoles in high yields with complete regioselectivity. The newly developed protocol also enabled the enantioselective preparation of chiral 4-acetyloxindole using a chiral iridium catalyst.

KW - C-C bond formation

KW - C-H functionalization

KW - Heterocycles

KW - Homogeneous catalysis

KW - Iridium

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DO - 10.1002/adsc.200900570

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JF - Advanced Synthesis and Catalysis

IS - 17

ER -

Iridium-catalyzed selective synthesis of 4-substituted benzofurans and indoles via directed cyclodehydration

Abstract

Keywords

ASJC Scopus subject areas

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