Abstract
π-Acidic metal-catalyzed cyclization reaction is one of the most efficient methods to construct highly elaborate molecular skeletons in a single operation under mild reaction conditions. These transformations often involve cleavage of σ bonds. Investigations into catalytic skeletal rearrangement have mainly utilized alkynylamines, alkynylalcohols, enynes, and propargylic esters as substrates. In this article, I report our recent findings on π-acidic metal catalyzed reactions via cleavage of σ bonds between major elements in body, such as carbon, nitrogen, oxygen, and sulfur, producing multisubstituted heterocycles in an atom efficient manner. That is, (a) catalytic carbon-heteroatom bond addition of ortho-alkynylphenyl ethers, -anilines, and -phenyl sulildes and (b) catalytic skeletal rearrangement of propargylic oximes.
Original language | English |
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Pages (from-to) | 581-592 |
Number of pages | 12 |
Journal | Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry |
Volume | 70 |
Issue number | 6 |
DOIs | |
Publication status | Published - 2012 Dec 1 |
Externally published | Yes |
Keywords
- 1-3 migration
- Alkyne activation
- Copper catalyst
- Gold catalyst
- Heteroarenes
- Metal carbenoid
- Oxime
- Platinum catalyst
- Skeletal rearrangement
- [2.3] rearrangement
ASJC Scopus subject areas
- Organic Chemistry