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The role of acetylides in dual gold catalysis: a mechanistic investigation of the selectivity difference in the naphthalene synthesis from diynes

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Under the conditions of dual activation catalysis with oxygen nucleophiles, β-substituted naphthalenes were obtained from 1,2-diethinyl arenes. Mechanistic studies, which include isotope labeling experiments, support that dual activation leads to β-substituted naphthalenes, whereas α-naphthalenes ar...

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Bibliographic Details
Main Authors: Graf, Katharina (Author) , Hindenberg, Philip (Author) , Tokimizu, Yusuke (Author) , Naoe, Saori (Author) , Rudolph, Matthias (Author) , Rominger, Frank (Author) , Ohno, Hiroaki (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: 8 January 2014
In: ChemCatChem
Year: 2014, Volume: 6, Issue: 1, Pages: 199-204
ISSN:1867-3899
DOI:10.1002/cctc.201300820
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/cctc.201300820
Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/cctc.201300820
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Author Notes:Katharina Graf, Philip D. Hindenberg, Yusuke Tokimizu, Saori Naoe, Matthias Rudolph, Frank Rominger, Hiroaki Ohno, and A. Stephen K. Hashmi
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Summary:Under the conditions of dual activation catalysis with oxygen nucleophiles, β-substituted naphthalenes were obtained from 1,2-diethinyl arenes. Mechanistic studies, which include isotope labeling experiments, support that dual activation leads to β-substituted naphthalenes, whereas α-naphthalenes are formed by π activation only, and no gold acetylide or dual activation is involved in the formation of the α-substituted products. Additional experiments on substrates that led to dibenzopentalenes support these mechanistic insights.
Item Description:Gesehen am 03.11.2020
Physical Description:Online Resource
ISSN:1867-3899
DOI:10.1002/cctc.201300820

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