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Inorganic Chemistry Frontiers Vol - 1 Issue - 4

Inorganic Chemistry Frontiers Vol - 1 Issue - 3

Inorganic Chemistry Frontiers Vol - 1 Issue - 2

Catalytic Sonogashira couplings mediated by an amido pincer complex of palladium

Content Provider	Royal Society of Chemistry (RSC)
Author	Hung, Yu-Ting Liang, Lan-Chang Liu, Yu-Sheng Chen, Ming-Tsz Kao, Ting-Yin Huang, Mei-Hui
Copyright Year	2014
Abstract	This work describes the efficacy of [PNP]PdCl (1a), where [PNP]− = bis(2-diphenylphosphinophenyl)amide, as a catalyst precursor for Csp–Csp2 bond-forming cross-coupling reactions of terminal alkynes with aryl halides in the presence of copper bromide and aliphatic amines in ethereal solutions under mild conditions. This catalysis is compatible with acetylenes that are alkyl, alkenyl, (hetero)aryl, or silyl substituted and aryl iodides or bromides that are electronically activated, neutral, or deactivated. The low reaction constants of 0.82(6) and 0.97(7) obtained from Hammett plots of competitive reactions employing electronically distinct aryl iodides and terminal alkynes, respectively, are likely suggestive of irrelevance of the rate-determining step in these catalytic transformations to oxidative addition of aryl halides or generation of mono-substituted acetylides. In sharp contrast, reactions employing a phosphorus-bound isopropyl derived 1b gave rather unsatisfactory results, highlighting a profound phosphorus substituent effect on this aryl alkynylation catalysis.
Starting Page	405
Ending Page	413
Page Count	9
File Format	HTM / HTML PDF
ISSN	20521553
Volume Number	1
Issue Number	5
Journal	Inorganic Chemistry Frontiers
DOI	10.1039/c3qi00086a
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Csp Hammett Amide Aryl Copper Haloalkane Aliphatic compound Alkyl Hammett equation Rate-determining step Oxidative addition Propyl group Phosphorus Substituent Alkynylation
Content Type	Text
Resource Type	Article
Subject	Inorganic Chemistry

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