Gold-catalyzed ring enlargement and cycloisomerization of alkynylamide tethered alkylidenecyclopropanes
Literature Information
Publication Date
2018-09-17
DOI
10.1039/C8QO00907D
Impact Factor
5.281
Authors
Jia-hao Zhang, Yin Wei
View Original
Abstract
Alkynylamide tethered alkylidenecyclopropanes 1 undergo gold(I)-catalyzed ring enlargement and cycloisomerization to yield two kinds of heterocyclic polycyclic products 2 and 3 in moderate to good yields depending on the use of different gold(I) catalysts. The use of PPh3AuCl/AgOTf as the catalyst afforded ring enlarged polycyclic products 2 and the use of JohnphosAuCl/NaBARF as the catalyst furnished ring enlarged spiropolycyclic products 3via a further intramolecular Friedel–Crafts reaction. A plausible reaction mechanism has also been proposed on the basis of previous literature. Moreover, a useful transformation of ring enlarged spiropolycyclic products 3 to a ring enlarged polycyclic product 4 has also been presented.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
![3,7-Di(1,1':3',1''-terphenyl-5'-yl)-10,11,12,13-tetrahydrodiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-ol 5-oxide structure](https://static.chemtradehub.com/structs/135/1352810-38-8-3f10.webp "3,7-Di(1,1':3',1''-terphenyl-5'-yl)-10,11,12,13-tetrahydrodiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-ol 5-oxide structure")
3,7-Di(1,1':3',1''-terphenyl-5'-yl)-10,11,12,13-tetrahydrodiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-ol 5-oxide
CAS Number:
1352810-38-8
Molecular Formula:
C53H39O4P
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