Synthesis of 5-Pyridyl-2-furaldehydes via palladium-catalyzed cross-coupling with triorganozincates

Donald R. Gauthier; Ronald H. Szumigala; Peter G. Dormer; Joseph D. Armstrong; R. P. Volante; Paul J. Reider

doi:10.1021/ol0170612

Synthesis of 5-Pyridyl-2-furaldehydes via palladium-catalyzed cross-coupling with triorganozincates

Donald R. Gauthier
, Ronald H. Szumigala
, Peter G. Dormer
, Joseph D. Armstrong
, R. P. Volante
, Paul J. Reider

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

63 Scopus citations

Abstract

(Equation Presented) 5-Pyridyl-and 5-aryl-2-furaldehydes are prepared from furaldehyde diethyl acetal in a four-step, one-pot procedure: (i) deprotonation; (2) Li to Zn transmetalation; (3) Pd-mediated cross-coupling; (4) aldehyde deprotection. Triorganozincate 7 was found to transfer all three groups in the Pd-catalyzed cross-coupling reaction with haloaromatics.

Original language	English (US)
Pages (from-to)	375-378
Number of pages	4
Journal	Organic letters
Volume	4
Issue number	3
DOIs	https://doi.org/10.1021/ol0170612
State	Published - Feb 7 2002
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0170612

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@article{c7582128fd6e4c2dbf8f37f2add77788,

title = "Synthesis of 5-Pyridyl-2-furaldehydes via palladium-catalyzed cross-coupling with triorganozincates",

abstract = "(Equation Presented) 5-Pyridyl-and 5-aryl-2-furaldehydes are prepared from furaldehyde diethyl acetal in a four-step, one-pot procedure: (i) deprotonation; (2) Li to Zn transmetalation; (3) Pd-mediated cross-coupling; (4) aldehyde deprotection. Triorganozincate 7 was found to transfer all three groups in the Pd-catalyzed cross-coupling reaction with haloaromatics.",

author = "Gauthier, \{Donald R.\} and Szumigala, \{Ronald H.\} and Dormer, \{Peter G.\} and Armstrong, \{Joseph D.\} and Volante, \{R. P.\} and Reider, \{Paul J.\}",

year = "2002",

month = feb,

day = "7",

doi = "10.1021/ol0170612",

language = "English (US)",

volume = "4",

pages = "375--378",

journal = "Organic letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "3",

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TY - JOUR

T1 - Synthesis of 5-Pyridyl-2-furaldehydes via palladium-catalyzed cross-coupling with triorganozincates

AU - Gauthier, Donald R.

AU - Szumigala, Ronald H.

AU - Dormer, Peter G.

AU - Armstrong, Joseph D.

AU - Volante, R. P.

AU - Reider, Paul J.

PY - 2002/2/7

Y1 - 2002/2/7

N2 - (Equation Presented) 5-Pyridyl-and 5-aryl-2-furaldehydes are prepared from furaldehyde diethyl acetal in a four-step, one-pot procedure: (i) deprotonation; (2) Li to Zn transmetalation; (3) Pd-mediated cross-coupling; (4) aldehyde deprotection. Triorganozincate 7 was found to transfer all three groups in the Pd-catalyzed cross-coupling reaction with haloaromatics.

AB - (Equation Presented) 5-Pyridyl-and 5-aryl-2-furaldehydes are prepared from furaldehyde diethyl acetal in a four-step, one-pot procedure: (i) deprotonation; (2) Li to Zn transmetalation; (3) Pd-mediated cross-coupling; (4) aldehyde deprotection. Triorganozincate 7 was found to transfer all three groups in the Pd-catalyzed cross-coupling reaction with haloaromatics.

UR - https://www.scopus.com/pages/publications/0000498440

UR - https://www.scopus.com/pages/publications/0000498440#tab=citedBy

U2 - 10.1021/ol0170612

DO - 10.1021/ol0170612

M3 - Article

C2 - 11820883

AN - SCOPUS:0000498440

SN - 1523-7060

VL - 4

SP - 375

EP - 378

JO - Organic letters

JF - Organic letters

IS - 3

ER -

Synthesis of 5-Pyridyl-2-furaldehydes via palladium-catalyzed cross-coupling with triorganozincates

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