Double Functionalization of Styrenes by Cu-Mediated Assisted Tandem Catalysis

Daichi Kawauchi; Hirofumi Ueda; Hidetoshi Tokuyama

doi:10.1002/ejoc.201900088

Double Functionalization of Styrenes by Cu-Mediated Assisted Tandem Catalysis

Daichi Kawauchi, Hirofumi Ueda, Hidetoshi Tokuyama

PHA - Molecular Pharmaceutical Science

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

10 Citations (Scopus)

Abstract

The double functionalization of styrenes through Cu-mediated assisted tandem catalysis was developed. The reaction was initiated by Cu-catalyzed aziridination and the subsequent nucleophilic ring-opening, which was triggered by the addition of (NH ₄ ) ₂ S ₂ O ₈ as an oxidant of Cu-catalyst to form a variety of C–C and C–X bonds. The expansion to three contiguous catalytic cycles led to the synthesis of functionalized indolines by one-pot operation.

Original language	English
Pages (from-to)	2056-2060
Number of pages	5
Journal	European Journal of Organic Chemistry
Volume	2019
Issue number	10
DOIs	https://doi.org/10.1002/ejoc.201900088
Publication status	Published - 2019 Mar 14

Keywords

Cu-catalysis
Double functionalization
Indolines
Spirocycle
Tandem catalysis

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201900088

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title = "Double Functionalization of Styrenes by Cu-Mediated Assisted Tandem Catalysis",

abstract = " The double functionalization of styrenes through Cu-mediated assisted tandem catalysis was developed. The reaction was initiated by Cu-catalyzed aziridination and the subsequent nucleophilic ring-opening, which was triggered by the addition of (NH 4 ) 2 S 2 O 8 as an oxidant of Cu-catalyst to form a variety of C–C and C–X bonds. The expansion to three contiguous catalytic cycles led to the synthesis of functionalized indolines by one-pot operation. ",

keywords = "Cu-catalysis, Double functionalization, Indolines, Spirocycle, Tandem catalysis",

author = "Daichi Kawauchi and Hirofumi Ueda and Hidetoshi Tokuyama",

note = "Funding Information: This work was supported by Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from AMED under Grant Number JP18am0101100, JSPS KAK-ENHI Grant Numbers JP18H04231 in Precisely Designed Catalysts with Customized Scaffolding and JP18H04642 in Hybrid Catalysis, a Grant-in aid for Scientific Research (B) (18H02549) and (C) (17K08204). Publisher Copyright: {\textcopyright} 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2019",

month = mar,

day = "14",

doi = "10.1002/ejoc.201900088",

language = "English",

volume = "2019",

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journal = "Justus Liebigs Annalen der Chemie",

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T1 - Double Functionalization of Styrenes by Cu-Mediated Assisted Tandem Catalysis

AU - Kawauchi, Daichi

AU - Ueda, Hirofumi

AU - Tokuyama, Hidetoshi

N1 - Funding Information: This work was supported by Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from AMED under Grant Number JP18am0101100, JSPS KAK-ENHI Grant Numbers JP18H04231 in Precisely Designed Catalysts with Customized Scaffolding and JP18H04642 in Hybrid Catalysis, a Grant-in aid for Scientific Research (B) (18H02549) and (C) (17K08204). Publisher Copyright: © 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2019/3/14

Y1 - 2019/3/14

N2 - The double functionalization of styrenes through Cu-mediated assisted tandem catalysis was developed. The reaction was initiated by Cu-catalyzed aziridination and the subsequent nucleophilic ring-opening, which was triggered by the addition of (NH 4 ) 2 S 2 O 8 as an oxidant of Cu-catalyst to form a variety of C–C and C–X bonds. The expansion to three contiguous catalytic cycles led to the synthesis of functionalized indolines by one-pot operation.

AB - The double functionalization of styrenes through Cu-mediated assisted tandem catalysis was developed. The reaction was initiated by Cu-catalyzed aziridination and the subsequent nucleophilic ring-opening, which was triggered by the addition of (NH 4 ) 2 S 2 O 8 as an oxidant of Cu-catalyst to form a variety of C–C and C–X bonds. The expansion to three contiguous catalytic cycles led to the synthesis of functionalized indolines by one-pot operation.

KW - Cu-catalysis

KW - Double functionalization

KW - Indolines

KW - Spirocycle

KW - Tandem catalysis

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DO - 10.1002/ejoc.201900088

M3 - Article

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VL - 2019

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EP - 2060

JO - Justus Liebigs Annalen der Chemie

JF - Justus Liebigs Annalen der Chemie

SN - 0075-4617

IS - 10

ER -

Double Functionalization of Styrenes by Cu-Mediated Assisted Tandem Catalysis

Abstract

Keywords

ASJC Scopus subject areas

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