2-Position-Selective C-H Perfluoroalkylation of Quinoline Derivatives

Takahiro Shirai; Motomu Kanai; Yoichiro Kuninobu

doi:10.1021/acs.orglett.8b00339

2-Position-Selective C-H Perfluoroalkylation of Quinoline Derivatives

Takahiro Shirai, Motomu Kanai, Yoichiro Kuninobu

Department of Fundamental Organic Chemistry

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

31 Citations (Scopus)

Abstract

We developed 2-position-selective, direct C-H trifluoromethylation, pentafluoroethylation, and heptafluoropropylation of quinoline derivatives. Regioselective transformation was achieved without derivatization of the quinolines. The reaction proceeded at room temperature with high functional group tolerance, even in gram scale. Notably, the reaction was applicable to substrates containing a functional group sensitive to oxidation and a drug molecule.

Original language	English
Pages (from-to)	1593-1596
Number of pages	4
Journal	Organic letters
Volume	20
Issue number	6
DOIs	https://doi.org/10.1021/acs.orglett.8b00339
Publication status	Published - Mar 16 2018

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.8b00339

Cite this

@article{489a1547426f4c91905fe8136d33254d,

title = "2-Position-Selective C-H Perfluoroalkylation of Quinoline Derivatives",

abstract = "We developed 2-position-selective, direct C-H trifluoromethylation, pentafluoroethylation, and heptafluoropropylation of quinoline derivatives. Regioselective transformation was achieved without derivatization of the quinolines. The reaction proceeded at room temperature with high functional group tolerance, even in gram scale. Notably, the reaction was applicable to substrates containing a functional group sensitive to oxidation and a drug molecule.",

author = "Takahiro Shirai and Motomu Kanai and Yoichiro Kuninobu",

note = "Funding Information: This work was supported in part by ERATO from JST (grant number: JPMJER1103), JSPS KAKENHI Grant Number JP 16K13946, and Yakugaku Shinkoukai. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = mar,

day = "16",

doi = "10.1021/acs.orglett.8b00339",

language = "English",

volume = "20",

pages = "1593--1596",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "6",

}

TY - JOUR

T1 - 2-Position-Selective C-H Perfluoroalkylation of Quinoline Derivatives

AU - Shirai, Takahiro

AU - Kanai, Motomu

AU - Kuninobu, Yoichiro

N1 - Funding Information: This work was supported in part by ERATO from JST (grant number: JPMJER1103), JSPS KAKENHI Grant Number JP 16K13946, and Yakugaku Shinkoukai. Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/3/16

Y1 - 2018/3/16

N2 - We developed 2-position-selective, direct C-H trifluoromethylation, pentafluoroethylation, and heptafluoropropylation of quinoline derivatives. Regioselective transformation was achieved without derivatization of the quinolines. The reaction proceeded at room temperature with high functional group tolerance, even in gram scale. Notably, the reaction was applicable to substrates containing a functional group sensitive to oxidation and a drug molecule.

AB - We developed 2-position-selective, direct C-H trifluoromethylation, pentafluoroethylation, and heptafluoropropylation of quinoline derivatives. Regioselective transformation was achieved without derivatization of the quinolines. The reaction proceeded at room temperature with high functional group tolerance, even in gram scale. Notably, the reaction was applicable to substrates containing a functional group sensitive to oxidation and a drug molecule.

UR - http://www.scopus.com/inward/record.url?scp=85044024236&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85044024236&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.8b00339

DO - 10.1021/acs.orglett.8b00339

M3 - Article

C2 - 29517241

AN - SCOPUS:85044024236

SN - 1523-7060

VL - 20

SP - 1593

EP - 1596

JO - Organic Letters

JF - Organic Letters

IS - 6

ER -

2-Position-Selective C-H Perfluoroalkylation of Quinoline Derivatives

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this