Atom-economical route to substituted pyridines via a scandium imide

Benjamin F. Wicker; Jennifer Scott; Alison R. Fout; Maren Pink; Daniel J. Mindiola

doi:10.1021/om2001537

Atom-economical route to substituted pyridines via a scandium imide

Benjamin F. Wicker, Jennifer Scott, Alison R. Fout, Maren Pink, Daniel J. Mindiola

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

Abstract

Taking advantage of a tautomerization process between (PNP)Sc - N(DIPP)(NC₅H₅) (PNP = N[2-P(CHMe₂) ₂-4-methylphenyl]₂^-, DIPP = 2,6-iPr ₂C₆H₃) and (PNP)Sc(NH(DIPP))(η²- NC₅H₄) (1), we demonstrate in this work that pyridine can be both activated and functionalized with isonitriles (in one case catalytically) to ultimately afford mono- and bis-imino-substituted pyridines. Several intermediates in the cycle have been isolated and characterized.

Original language	English (US)
Pages (from-to)	2453-2456
Number of pages	4
Journal	Organometallics
Volume	30
Issue number	9
DOIs	https://doi.org/10.1021/om2001537
State	Published - May 9 2011
Externally published	Yes

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Online availability

10.1021/om2001537

Library availability

Discover UIUC Full Text

Cite this

@article{ee56699f5c3a4cd081f9ebcf9036279c,

title = "Atom-economical route to substituted pyridines via a scandium imide",

abstract = "Taking advantage of a tautomerization process between (PNP)Sc - N(DIPP)(NC5H5) (PNP = N[2-P(CHMe2) 2-4-methylphenyl]2-, DIPP = 2,6-iPr 2C6H3) and (PNP)Sc(NH(DIPP))(η2- NC5H4) (1), we demonstrate in this work that pyridine can be both activated and functionalized with isonitriles (in one case catalytically) to ultimately afford mono- and bis-imino-substituted pyridines. Several intermediates in the cycle have been isolated and characterized.",

author = "Wicker, {Benjamin F.} and Jennifer Scott and Fout, {Alison R.} and Maren Pink and Mindiola, {Daniel J.}",

year = "2011",

month = may,

day = "9",

doi = "10.1021/om2001537",

language = "English (US)",

volume = "30",

pages = "2453--2456",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "9",

}

TY - JOUR

T1 - Atom-economical route to substituted pyridines via a scandium imide

AU - Wicker, Benjamin F.

AU - Scott, Jennifer

AU - Fout, Alison R.

AU - Pink, Maren

AU - Mindiola, Daniel J.

PY - 2011/5/9

Y1 - 2011/5/9

N2 - Taking advantage of a tautomerization process between (PNP)Sc - N(DIPP)(NC5H5) (PNP = N[2-P(CHMe2) 2-4-methylphenyl]2-, DIPP = 2,6-iPr 2C6H3) and (PNP)Sc(NH(DIPP))(η2- NC5H4) (1), we demonstrate in this work that pyridine can be both activated and functionalized with isonitriles (in one case catalytically) to ultimately afford mono- and bis-imino-substituted pyridines. Several intermediates in the cycle have been isolated and characterized.

AB - Taking advantage of a tautomerization process between (PNP)Sc - N(DIPP)(NC5H5) (PNP = N[2-P(CHMe2) 2-4-methylphenyl]2-, DIPP = 2,6-iPr 2C6H3) and (PNP)Sc(NH(DIPP))(η2- NC5H4) (1), we demonstrate in this work that pyridine can be both activated and functionalized with isonitriles (in one case catalytically) to ultimately afford mono- and bis-imino-substituted pyridines. Several intermediates in the cycle have been isolated and characterized.

UR - http://www.scopus.com/inward/record.url?scp=79955634119&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79955634119&partnerID=8YFLogxK

U2 - 10.1021/om2001537

DO - 10.1021/om2001537

M3 - Article

AN - SCOPUS:79955634119

SN - 0276-7333

VL - 30

SP - 2453

EP - 2456

JO - Organometallics

JF - Organometallics

IS - 9

ER -

Atom-economical route to substituted pyridines via a scandium imide

Abstract

ASJC Scopus subject areas

Online availability

Library availability

Related links

Fingerprint

Cite this