A metal-, oxidant-, and fluorous solvent-free synthesis of α-indolylketones enabled by an umpolung strategy

Takumi Abe; Seiya Hirao; Toshiki Yamashiro

doi:10.1039/d0cc04795c

A metal-, oxidant-, and fluorous solvent-free synthesis of α-indolylketones enabled by an umpolung strategy

Takumi Abe, Seiya Hirao, Toshiki Yamashiro

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

7 Citations (Scopus)

Abstract

Enamines undergo α-indolization with ammonium salts in the presence of Et₃N to form α-indolylketones. This is the first example of transition metal-, oxidant-, and fluorous solvent-free α-indolization of ketones. Key to the success of this convenient protocol was the use ofin situgenerated electrophilic indole species, as well as the use of enamines as a ketone enolate equivalent.

Original language	English
Pages (from-to)	10183-10186
Number of pages	4
Journal	Chemical Communications
Volume	56
Issue number	70
DOIs	https://doi.org/10.1039/d0cc04795c
Publication status	Published - Sept 11 2020
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

Access to Document

10.1039/d0cc04795c

Cite this

@article{475c55ef924b42aaa2480e588c126a7b,

title = "A metal-, oxidant-, and fluorous solvent-free synthesis of α-indolylketones enabled by an umpolung strategy",

abstract = "Enamines undergo α-indolization with ammonium salts in the presence of Et3N to form α-indolylketones. This is the first example of transition metal-, oxidant-, and fluorous solvent-free α-indolization of ketones. Key to the success of this convenient protocol was the use ofin situgenerated electrophilic indole species, as well as the use of enamines as a ketone enolate equivalent.",

author = "Takumi Abe and Seiya Hirao and Toshiki Yamashiro",

note = "Funding Information: This work was financially supported by JSPS (KAKENHI Grant Number 16K18849 for T.A.) as a Grant-in-Aid for Young Scientists (B). Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2020.",

year = "2020",

month = sep,

day = "11",

doi = "10.1039/d0cc04795c",

language = "English",

volume = "56",

pages = "10183--10186",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "70",

}

TY - JOUR

T1 - A metal-, oxidant-, and fluorous solvent-free synthesis of α-indolylketones enabled by an umpolung strategy

AU - Abe, Takumi

AU - Hirao, Seiya

AU - Yamashiro, Toshiki

N1 - Funding Information: This work was financially supported by JSPS (KAKENHI Grant Number 16K18849 for T.A.) as a Grant-in-Aid for Young Scientists (B). Publisher Copyright: © The Royal Society of Chemistry 2020.

PY - 2020/9/11

Y1 - 2020/9/11

N2 - Enamines undergo α-indolization with ammonium salts in the presence of Et3N to form α-indolylketones. This is the first example of transition metal-, oxidant-, and fluorous solvent-free α-indolization of ketones. Key to the success of this convenient protocol was the use ofin situgenerated electrophilic indole species, as well as the use of enamines as a ketone enolate equivalent.

AB - Enamines undergo α-indolization with ammonium salts in the presence of Et3N to form α-indolylketones. This is the first example of transition metal-, oxidant-, and fluorous solvent-free α-indolization of ketones. Key to the success of this convenient protocol was the use ofin situgenerated electrophilic indole species, as well as the use of enamines as a ketone enolate equivalent.

UR - http://www.scopus.com/inward/record.url?scp=85090250957&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85090250957&partnerID=8YFLogxK

U2 - 10.1039/d0cc04795c

DO - 10.1039/d0cc04795c

M3 - Article

C2 - 32748921

AN - SCOPUS:85090250957

SN - 1359-7345

VL - 56

SP - 10183

EP - 10186

JO - Chemical Communications

JF - Chemical Communications

IS - 70

ER -

A metal-, oxidant-, and fluorous solvent-free synthesis of α-indolylketones enabled by an umpolung strategy

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this