Insertion of arynes into thioureas: A new amidine synthesis

Kallolmay Biswas; Michael F. Greaney

doi:10.1021/ol202049v

Insertion of arynes into thioureas: A new amidine synthesis

Kallolmay Biswas
, Michael F. Greaney

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

Abstract

Arynes, generated from trimethylsilyl phenyltriflate precursors, have been found to react with thioureas via a formal π-insertion into the C=S bond. The reaction contrasts with that of ureas, which proceeds via benzyne σ-insertion into the C-N bond, and represents a new, operationally simple route to functionalized amidines. © 2011 American Chemical Society.

Original language	English
Pages (from-to)	4946-4949
Number of pages	3
Journal	Organic Letters
Volume	13
Issue number	18
DOIs	https://doi.org/10.1021/ol202049v
Publication status	Published - 16 Sept 2011

Access to Document

10.1021/ol202049v

Cite this

@article{5739595cee4e4a358c799b3ce70b2769,

title = "Insertion of arynes into thioureas: A new amidine synthesis",

abstract = "Arynes, generated from trimethylsilyl phenyltriflate precursors, have been found to react with thioureas via a formal π-insertion into the C=S bond. The reaction contrasts with that of ureas, which proceeds via benzyne σ-insertion into the C-N bond, and represents a new, operationally simple route to functionalized amidines. {\textcopyright} 2011 American Chemical Society.",

author = "Kallolmay Biswas and Greaney, \{Michael F.\}",

note = "CAPLUS AN 2011:1050837(Journal; Online Computer File)",

year = "2011",

month = sep,

day = "16",

doi = "10.1021/ol202049v",

language = "English",

volume = "13",

pages = "4946--4949",

journal = "Organic Letters",

issn = "1523-7052",

publisher = "American Chemical Society",

number = "18",

}

TY - JOUR

T1 - Insertion of arynes into thioureas: A new amidine synthesis

AU - Biswas, Kallolmay

AU - Greaney, Michael F.

N1 - CAPLUS AN 2011:1050837(Journal; Online Computer File)

PY - 2011/9/16

Y1 - 2011/9/16

N2 - Arynes, generated from trimethylsilyl phenyltriflate precursors, have been found to react with thioureas via a formal π-insertion into the C=S bond. The reaction contrasts with that of ureas, which proceeds via benzyne σ-insertion into the C-N bond, and represents a new, operationally simple route to functionalized amidines. © 2011 American Chemical Society.

AB - Arynes, generated from trimethylsilyl phenyltriflate precursors, have been found to react with thioureas via a formal π-insertion into the C=S bond. The reaction contrasts with that of ureas, which proceeds via benzyne σ-insertion into the C-N bond, and represents a new, operationally simple route to functionalized amidines. © 2011 American Chemical Society.

U2 - 10.1021/ol202049v

DO - 10.1021/ol202049v

M3 - Article

SN - 1523-7052

VL - 13

SP - 4946

EP - 4949

JO - Organic Letters

JF - Organic Letters

IS - 18

ER -

Insertion of arynes into thioureas: A new amidine synthesis

Abstract

Access to Document

Fingerprint

Cite this