Different selectivities in the insertions into C(sp2)-H bonds: Benzofulvenes by dual Gold catalysis competition experiments
An unprecedented, often almost quantitative access to tricyclic aromatic compounds by dual gold catalysis was developed. This synthetic route expands the scope of benzofulvene derivatives through a C(sp2)-H bond insertion in easily available starting materials. The insertion takes place with an excl...
Saved in:
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article (Journal) |
| Language: | English |
| Published: |
July 25, 2018
|
| In: |
Chemistry - a European journal
Year: 2018, Volume: 24, Issue: 42, Pages: 10766-10772 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201801031 |
| Online Access: | Resolving-System, Volltext: http://dx.doi.org/10.1002/chem.201801031 Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201801031 
|
| Author Notes: | Alex J. Plajer, Lukas Ahrens, Marcel Wieteck, Danilo M. Lustosa, Rasool Babaahmadi, Brian Yates, Alireza Ariafard, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi |
MARC
| LEADER | 00000caa a2200000 c 4500 | ||
|---|---|---|---|
| 001 | 1585087831 | ||
| 003 | DE-627 | ||
| 005 | 20230427161343.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 181211s2018 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1002/chem.201801031 |2 doi | |
| 035 | |a (DE-627)1585087831 | ||
| 035 | |a (DE-576)515087831 | ||
| 035 | |a (DE-599)BSZ515087831 | ||
| 035 | |a (OCoLC)1341024981 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rda | ||
| 041 | |a eng | ||
| 084 | |a 30 |2 sdnb | ||
| 100 | 1 | |a Plajer, Alex |e VerfasserIn |0 (DE-588)1160537194 |0 (DE-627)102380719X |0 (DE-576)505981157 |4 aut | |
| 245 | 1 | 0 | |a Different selectivities in the insertions into C(sp2)-H bonds |b Benzofulvenes by dual Gold catalysis competition experiments |c Alex J. Plajer, Lukas Ahrens, Marcel Wieteck, Danilo M. Lustosa, Rasool Babaahmadi, Brian Yates, Alireza Ariafard, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi |
| 264 | 1 | |c July 25, 2018 | |
| 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 Im Titel ist die Ziffer 2 hochgestellt | ||
| 500 | |a Gesehen am 11.12.2018 | ||
| 520 | |a An unprecedented, often almost quantitative access to tricyclic aromatic compounds by dual gold catalysis was developed. This synthetic route expands the scope of benzofulvene derivatives through a C(sp2)-H bond insertion in easily available starting materials. The insertion takes place with an exclusive chemoselectivity with respect to the competing aromatic C-H positions. A bidirectional synthesis with two competing ortho-aryl C-H bonds in the selectivity-determining step also shows perfect selectivity; this result is explained by a computational investigation of the two conceivable intermediates. The intramolecular competition of two non-equivalent aryl C-H bonds with a benzylic methyl group also showed perfect selectivity. | ||
| 650 | 4 | |a benzofulvenes | |
| 650 | 4 | |a C−H insertion | |
| 650 | 4 | |a chemoselectivity | |
| 650 | 4 | |a dual gold catalysis | |
| 650 | 4 | |a gold vinylidenes | |
| 700 | 1 | |a Ahrens, Lukas |d 1992- |e VerfasserIn |0 (DE-588)1173201718 |0 (DE-627)1042346194 |0 (DE-576)515087661 |4 aut | |
| 700 | 1 | |a Wieteck, Marcel |e VerfasserIn |0 (DE-588)102524852X |0 (DE-627)721919014 |0 (DE-576)370118707 |4 aut | |
| 700 | 1 | |a Lustosa, Danilo Machado |e VerfasserIn |0 (DE-588)1176431498 |0 (DE-627)1047423510 |0 (DE-576)51661858X |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 | |
| 700 | 1 | |a Hashmi, A. Stephen K. |d 1963- |e VerfasserIn |0 (DE-588)101199576X |0 (DE-627)704823926 |0 (DE-576)169176665 |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Chemistry - a European journal |d Weinheim : Wiley-VCH, 1995 |g 24(2018), 42, Seite 10766-10772 |h Online-Ressource |w (DE-627)270935193 |w (DE-600)1478547-X |w (DE-576)078707404 |x 1521-3765 |7 nnas |a Different selectivities in the insertions into C(sp2)-H bonds Benzofulvenes by dual Gold catalysis competition experiments |
| 773 | 1 | 8 | |g volume:24 |g year:2018 |g number:42 |g pages:10766-10772 |g extent:7 |a Different selectivities in the insertions into C(sp2)-H bonds Benzofulvenes by dual Gold catalysis competition experiments |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1002/chem.201801031 |x Resolving-System |x Verlag |3 Volltext |
| 856 | 4 | 0 | |u https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201801031 |x Verlag |3 Volltext |
| 951 | |a AR | ||
| 992 | |a 20181211 | ||
| 993 | |a Article | ||
| 994 | |a 2018 | ||
| 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 10 |y j | ||
| 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 9 | ||
| 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 8 | ||
| 998 | |g 102524852X |a Wieteck, Marcel |m 102524852X:Wieteck, Marcel |d 120000 |d 120100 |e 120000PW102524852X |e 120100PW102524852X |k 0/120000/ |k 1/120000/120100/ |p 3 | ||
| 998 | |g 1173201718 |a Ahrens, Lukas |m 1173201718:Ahrens, Lukas |d 120000 |d 120100 |e 120000PA1173201718 |e 120100PA1173201718 |k 0/120000/ |k 1/120000/120100/ |p 2 | ||
| 999 | |a KXP-PPN1585087831 |e 3037394544 | ||
| BIB | |a Y | ||
| SER | |a journal | ||
| JSO | |a {"language":["eng"],"recId":"1585087831","note":["Im Titel ist die Ziffer 2 hochgestellt","Gesehen am 11.12.2018"],"origin":[{"dateIssuedDisp":"July 25, 2018","dateIssuedKey":"2018"}],"name":{"displayForm":["Alex J. Plajer, Lukas Ahrens, Marcel Wieteck, Danilo M. Lustosa, Rasool Babaahmadi, Brian Yates, Alireza Ariafard, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi"]},"id":{"doi":["10.1002/chem.201801031"],"eki":["1585087831"]},"type":{"bibl":"article-journal","media":"Online-Ressource"},"physDesc":[{"extent":"7 S."}],"relHost":[{"title":[{"title_sort":"Chemistry - a European journal","title":"Chemistry - a European journal"}],"physDesc":[{"extent":"Online-Ressource"}],"type":{"bibl":"periodical","media":"Online-Ressource"},"id":{"eki":["270935193"],"doi":["10.1002/(ISSN)1521-3765"],"issn":["1521-3765"],"zdb":["1478547-X"]},"pubHistory":["1.1995 -"],"disp":"Different selectivities in the insertions into C(sp2)-H bonds Benzofulvenes by dual Gold catalysis competition experimentsChemistry - a European journal","origin":[{"publisherPlace":"Weinheim","dateIssuedDisp":"1995-","publisher":"Wiley-VCH","dateIssuedKey":"1995"}],"part":{"pages":"10766-10772","issue":"42","extent":"7","text":"24(2018), 42, Seite 10766-10772","volume":"24","year":"2018"},"note":["Fortsetzung der Druck-Ausgabe","Gesehen am 27. Februar 2017"],"language":["eng"],"recId":"270935193"}],"title":[{"subtitle":"Benzofulvenes by dual Gold catalysis competition experiments","title_sort":"Different selectivities in the insertions into C(sp2)-H bonds","title":"Different selectivities in the insertions into C(sp2)-H bonds"}],"person":[{"role":"aut","given":"Alex","family":"Plajer","display":"Plajer, Alex"},{"given":"Lukas","role":"aut","display":"Ahrens, Lukas","family":"Ahrens"},{"role":"aut","given":"Marcel","family":"Wieteck","display":"Wieteck, Marcel"},{"role":"aut","given":"Danilo Machado","family":"Lustosa","display":"Lustosa, Danilo Machado"},{"family":"Rudolph","display":"Rudolph, Matthias","role":"aut","given":"Matthias"},{"display":"Rominger, Frank","family":"Rominger","given":"Frank","role":"aut"},{"given":"A. Stephen K.","role":"aut","display":"Hashmi, A. Stephen K.","family":"Hashmi"}]} | ||
| SRT | |a PLAJERALEXDIFFERENTS2520 | ||