Gold catalysis: domino reaction of en-diynes to highly substituted phenols

By Sonogashira coupling of 1,7-heptadiynes and 1,8-octadiynes with 2-iodoallyl alcohols, various substrates that bear a 2-alkynylallyl alcohol moiety tethered to an additional alkyne were prepared in one step. Subjection to nitrogen acyclic carbene (NAC)/gold(I) catalysts delivered highly substitute...

Full description

Saved in:
Bibliographic Details
Main Authors: Hashmi, A. Stephen K. (Author) , Häffner, Tobias (Author) , Rudolph, Matthias (Author) , Rominger, Frank (Author)
Format: Article (Journal)
Language:English
Published: 07 June 2011
In: Chemistry - a European journal
Year: 2011, Volume: 17, Issue: 29, Pages: 8195-8201
ISSN:1521-3765
DOI:10.1002/chem.201100305
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chem.201100305
Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201100305
Get full text
Author Notes:A. Stephen K. Hashmi, Tobias Häffner, Matthias Rudolph, and Frank Rominger

MARC

LEADER 00000caa a2200000 c 4500
001 1815457708
003 DE-627
005 20230710121322.0
007 cr uuu---uuuuu
008 220831s2011 xx |||||o 00| ||eng c
024 7 |a 10.1002/chem.201100305  |2 doi 
035 |a (DE-627)1815457708 
035 |a (DE-599)KXP1815457708 
035 |a (OCoLC)1389793076 
040 |a DE-627  |b ger  |c DE-627  |e rda 
041 |a eng 
084 |a 30  |2 sdnb 
100 1 |a Hashmi, A. Stephen K.  |d 1963-  |e VerfasserIn  |0 (DE-588)101199576X  |0 (DE-627)704823926  |0 (DE-576)169176665  |4 aut 
245 1 0 |a Gold catalysis  |b domino reaction of en-diynes to highly substituted phenols  |c A. Stephen K. Hashmi, Tobias Häffner, Matthias Rudolph, and Frank Rominger 
264 1 |c 07 June 2011 
300 |a 7 
336 |a Text  |b txt  |2 rdacontent 
337 |a Computermedien  |b c  |2 rdamedia 
338 |a Online-Ressource  |b cr  |2 rdacarrier 
500 |a Gesehen am 31.08.2022 
520 |a By Sonogashira coupling of 1,7-heptadiynes and 1,8-octadiynes with 2-iodoallyl alcohols, various substrates that bear a 2-alkynylallyl alcohol moiety tethered to an additional alkyne were prepared in one step. Subjection to nitrogen acyclic carbene (NAC)/gold(I) catalysts delivered highly substituted phenols in an efficient domino reaction. Furan derivatives were formed as intermediates; this was proven by in situ NMR spectroscopy. The uncommon substitution pattern of these furans opens the way for a selective formation of phenols that contain the hydroxyl group in the meta position to the ring junction, which previously was not possible by gold-catalyzed furan-yne cyclization. Furthermore, interesting mechanistic insights were obtained by products derived from secondary allyl alcohols. In this case, in addition to the phenolic compounds, a ketone is formed by 1,2-alkyl shift. 
650 4 |a alkynes 
650 4 |a domino reactions 
650 4 |a furans 
650 4 |a gold 
650 4 |a phenols 
700 1 |a Häffner, Tobias  |e VerfasserIn  |0 (DE-588)1019978546  |0 (DE-627)691067910  |0 (DE-576)260183962  |4 aut 
700 1 |a Rudolph, Matthias  |d 1975-  |e VerfasserIn  |0 (DE-588)136790380  |0 (DE-627)587252405  |0 (DE-576)301277524  |4 aut 
700 1 |a Rominger, Frank  |d 1964-  |e VerfasserIn  |0 (DE-588)1019978228  |0 (DE-627)691067821  |0 (DE-576)359202756  |4 aut 
773 0 8 |i Enthalten in  |t Chemistry - a European journal  |d Weinheim : Wiley-VCH, 1995  |g 17(2011), 29, Seite 8195-8201  |h Online-Ressource  |w (DE-627)270935193  |w (DE-600)1478547-X  |w (DE-576)078707404  |x 1521-3765  |7 nnas  |a Gold catalysis domino reaction of en-diynes to highly substituted phenols 
773 1 8 |g volume:17  |g year:2011  |g number:29  |g pages:8195-8201  |g extent:7  |a Gold catalysis domino reaction of en-diynes to highly substituted phenols 
776 0 8 |i Erscheint auch als  |n Druck-Ausgabe  |t Gold catalysis  |d 2011  |w (DE-627)1634433017  |w (DE-576)370196287 
856 4 0 |u https://doi.org/10.1002/chem.201100305  |x Verlag  |x Resolving-System  |z lizenzpflichtig  |3 Volltext 
856 4 0 |u https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201100305  |x Verlag  |z lizenzpflichtig  |3 Volltext 
951 |a AR 
992 |a 20220831 
993 |a Article 
994 |a 2011 
998 |g 136790380  |a Rudolph, Matthias  |m 136790380:Rudolph, Matthias  |d 120000  |d 120100  |e 120000PR136790380  |e 120100PR136790380  |k 0/120000/  |k 1/120000/120100/  |p 3 
998 |g 1019978228  |a Rominger, Frank  |m 1019978228:Rominger, Frank  |d 120000  |d 120100  |e 120000PR1019978228  |e 120100PR1019978228  |k 0/120000/  |k 1/120000/120100/  |p 4  |y j 
998 |g 1019978546  |a Häffner, Tobias  |m 1019978546:Häffner, Tobias  |d 120000  |d 500000  |d 500623  |e 120000PH1019978546  |e 500000PH1019978546  |e 500623PH1019978546  |k 0/120000/  |k 0/500000/  |k 1/500000/500623/  |p 2 
998 |g 101199576X  |a Hashmi, A. Stephen K.  |m 101199576X:Hashmi, A. Stephen K.  |d 120000  |d 120100  |e 120000PH101199576X  |e 120100PH101199576X  |k 0/120000/  |k 1/120000/120100/  |p 1  |x j 
999 |a KXP-PPN1815457708  |e 4183762820 
BIB |a Y 
SER |a journal 
JSO |a {"physDesc":[{"extent":"7 S."}],"relHost":[{"id":{"issn":["1521-3765"],"zdb":["1478547-X"],"eki":["270935193"],"doi":["10.1002/(ISSN)1521-3765"]},"origin":[{"dateIssuedDisp":"1995-","publisher":"Wiley-VCH","dateIssuedKey":"1995","publisherPlace":"Weinheim"}],"physDesc":[{"extent":"Online-Ressource"}],"title":[{"title":"Chemistry - a European journal","title_sort":"Chemistry - a European journal"}],"language":["eng"],"recId":"270935193","note":["Fortsetzung der Druck-Ausgabe","Gesehen am 27. Februar 2017"],"type":{"media":"Online-Ressource","bibl":"periodical"},"disp":"Gold catalysis domino reaction of en-diynes to highly substituted phenolsChemistry - a European journal","part":{"extent":"7","text":"17(2011), 29, Seite 8195-8201","volume":"17","issue":"29","pages":"8195-8201","year":"2011"},"pubHistory":["1.1995 -"]}],"name":{"displayForm":["A. Stephen K. Hashmi, Tobias Häffner, Matthias Rudolph, and Frank Rominger"]},"origin":[{"dateIssuedDisp":"07 June 2011","dateIssuedKey":"2011"}],"id":{"doi":["10.1002/chem.201100305"],"eki":["1815457708"]},"note":["Gesehen am 31.08.2022"],"type":{"media":"Online-Ressource","bibl":"article-journal"},"recId":"1815457708","language":["eng"],"person":[{"display":"Hashmi, A. Stephen K.","roleDisplay":"VerfasserIn","role":"aut","family":"Hashmi","given":"A. Stephen K."},{"roleDisplay":"VerfasserIn","display":"Häffner, Tobias","role":"aut","family":"Häffner","given":"Tobias"},{"family":"Rudolph","given":"Matthias","display":"Rudolph, Matthias","roleDisplay":"VerfasserIn","role":"aut"},{"role":"aut","roleDisplay":"VerfasserIn","display":"Rominger, Frank","given":"Frank","family":"Rominger"}],"title":[{"subtitle":"domino reaction of en-diynes to highly substituted phenols","title":"Gold catalysis","title_sort":"Gold catalysis"}]} 
SRT |a HASHMIASTEGOLDCATALY0720