Triflic acid-catalyzed C sp3 - H functionalization of 2-methyl azaarenes with a α-trifluoromethyl imino ester

Mark Blocker; Supriya Immaneni; Abid Shaikh

doi:10.1016/j.tetlet.2014.08.061

Triflic acid-catalyzed C sp³ - H functionalization of 2-methyl azaarenes with a α-trifluoromethyl imino ester

Mark Blocker, Supriya Immaneni, Abid Shaikh

Biochemistry, Chemistry & Physics

Georgia Southern University

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

21 Scopus citations

Abstract

A Brønsted acid promoted C_sp³-H functionalization of 2-alkyl azaarenes with α-trifluoromethylated imino ester is described. A catalytic amount of triflic acid provided straightforward access to the corresponding trifluoromethylated amino esters via concomitant in situ one step N-alkyl deprotection. On further hydrolysis of ester, synthesis of quinoline derived unnatural trifluoromethylated amino acids has been achieved in a short and efficient manner.

Original language	English
Pages (from-to)	5572-5575
Number of pages	4
Journal	Tetrahedron Letters
Volume	55
Issue number	40
DOIs	https://doi.org/10.1016/j.tetlet.2014.08.061
State	Published - Oct 1 2014

Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Azaarenes
Brønsted acid
C-H functionalization
Triflic acid
Trifluoromethyl imino ester

Access to Document

10.1016/j.tetlet.2014.08.061

Cite this

@article{8e157625708f48c395ab3642dd2fd4af,

title = "Triflic acid-catalyzed C sp3 - H functionalization of 2-methyl azaarenes with a α-trifluoromethyl imino ester",

abstract = "A Br{\o}nsted acid promoted Csp3-H functionalization of 2-alkyl azaarenes with α-trifluoromethylated imino ester is described. A catalytic amount of triflic acid provided straightforward access to the corresponding trifluoromethylated amino esters via concomitant in situ one step N-alkyl deprotection. On further hydrolysis of ester, synthesis of quinoline derived unnatural trifluoromethylated amino acids has been achieved in a short and efficient manner.",

keywords = "Azaarenes, Br{\o}nsted acid, C-H functionalization, Triflic acid, Trifluoromethyl imino ester",

author = "Mark Blocker and Supriya Immaneni and Abid Shaikh",

year = "2014",

month = oct,

day = "1",

doi = "10.1016/j.tetlet.2014.08.061",

language = "English",

volume = "55",

pages = "5572--5575",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "40",

}

TY - JOUR

T1 - Triflic acid-catalyzed C sp3 - H functionalization of 2-methyl azaarenes with a α-trifluoromethyl imino ester

AU - Blocker, Mark

AU - Immaneni, Supriya

AU - Shaikh, Abid

PY - 2014/10/1

Y1 - 2014/10/1

N2 - A Brønsted acid promoted Csp3-H functionalization of 2-alkyl azaarenes with α-trifluoromethylated imino ester is described. A catalytic amount of triflic acid provided straightforward access to the corresponding trifluoromethylated amino esters via concomitant in situ one step N-alkyl deprotection. On further hydrolysis of ester, synthesis of quinoline derived unnatural trifluoromethylated amino acids has been achieved in a short and efficient manner.

AB - A Brønsted acid promoted Csp3-H functionalization of 2-alkyl azaarenes with α-trifluoromethylated imino ester is described. A catalytic amount of triflic acid provided straightforward access to the corresponding trifluoromethylated amino esters via concomitant in situ one step N-alkyl deprotection. On further hydrolysis of ester, synthesis of quinoline derived unnatural trifluoromethylated amino acids has been achieved in a short and efficient manner.

KW - Azaarenes

KW - Brønsted acid

KW - C-H functionalization

KW - Triflic acid

KW - Trifluoromethyl imino ester

UR - http://www.scopus.com/inward/record.url?scp=84908672374&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2014.08.061

DO - 10.1016/j.tetlet.2014.08.061

M3 - Article

AN - SCOPUS:84908672374

SN - 0040-4039

VL - 55

SP - 5572

EP - 5575

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 40

ER -