DOI: 10.1002/anie.200600571. Au<sup>I</sup>‐Catalyzed Tandem [3,3] Rearrangement–Intramolecular Hydroarylation: Mild and Efficient Formation of Substituted Indenes

AuI‐Catalyzed Tandem [3,3] Rearrangement–Intramolecular Hydroarylation: Mild and Efficient Formation of Substituted Indenes

10.1002/anie.200600571

Crossref journal-article

Wiley

Angewandte Chemie International Edition (311)

Bibliography

Marion, N., DÃezâGonzÃ¡lez, S., de FrÃ©mont, P., Noble, A. R., & Nolan, S. P. (2006). AuIâCatalyzed Tandem [3,3] RearrangementâIntramolecular Hydroarylation: Mild and Efficient Formation of Substituted Indenes. Angewandte Chemie International Edition, 45(22), 3647â3650. Portico.

Authors 5

Nicolas Marion (first)
Silvia Díez‐González (additional)
Pierre de Frémont (additional)
April R. Noble (additional)
Steven P. Nolan (additional)

References 66 Referenced 311

For recent reviews on gold‐catalyzed reactions see:
10.1039/B416516K
{'key': 'e_1_2_3_3_2', 'first-page': '7150', 'author': 'Hashmi A. S. K.', 'journal-title': 'Angew. Chem. 2005, 117'} / Angew. Chem. 2005, 117 by Hashmi A. S. K.
10.1002/anie.200502735
For recent contributions on gold‐catalyzed enyne cycloisomerization see:
10.1021/ja046248w
10.1021/ja046112y
10.1021/ja042257t
10.1021/ol0515917
10.1002/ange.200503484
10.1002/anie.200503484
10.1002/chem.200501089
10.1055/s-2006-926261
10.1002/chem.200501299
{'key': 'e_1_2_3_14_2', 'first-page': '167', 'author': 'Nevado C.', 'year': '2005', 'journal-title': 'Synthesis'} / Synthesis by Nevado C. (2005)
{'key': 'e_1_2_3_15_2', 'first-page': '2397', 'volume': '13', 'author': 'Korte A.', 'year': '2004', 'journal-title': 'Synlett'} / Synlett by Korte A. (2004)
10.1002/(SICI)1521-3757(19980202)110:3<308::AID-ANGE308>3.0.CO;2-V
10.1002/(SICI)1521-3773(19980216)37:3<296::AID-ANIE296>3.0.CO;2-U
10.1021/jo991140y
For recent selected reports on indene formation see:
10.1021/jo025828d
10.1021/jo049722p
10.1021/jo049506g
10.1021/ja045516n
10.1021/ol0498242
10.1021/ja051114j
10.1021/ja0528174
10.1021/ol051907a
10.1021/ja0552500
10.1021/ja048094q
Ruthenium‐catalyzed:
10.1021/jo034841a
10.1021/ja053192c
10.1002/hlca.19730560309
10.1021/om050111c
10.1021/ja0438821
For details see the Supporting Information.
Characteristic signals for the expected indene could be observed in the1H NMR spectrum of the crude reaction mixture and accounted for <5 % of the signal intensity but this product could not be cleanly isolated.
Compounds2 hand3 hwere easily separated by flash chromatography.
For selected examples of intramolecular electrophilic activation of an alkyne toward aromatic substitution see:
10.1021/ja961107i
10.1126/science.287.5460.1992
10.1021/jo016232d
10.1021/jo025962y
10.1002/chem.200401069
10.1002/ejoc.200300260
10.1021/ja057127e
For examples of gold‐catalyzed activation of allenes see:
10.1002/1521-3757(20000703)112:13<2382::AID-ANGE2382>3.0.CO;2-R
10.1002/1521-3773(20000703)39:13<2285::AID-ANIE2285>3.0.CO;2-F
10.1021/ol016205
10.1021/ol0481838
10.1021/ja053290y
10.1021/ja056419c
10.1021/ja057327q
Intramolecular hydroarylation of aryl allenes leading to indenes can be catalyzed by strongly acidic media by metals (Al Rh Co) or photochemically and usually requires high temperature and/or a prolonged reaction time for a moderate chemical yield; for reviews see:
10.1021/cr60247a004
{'key': 'e_1_2_3_57_2', 'volume-title': 'Allenes in Organic Synthesis', 'year': '1984'} / Allenes in Organic Synthesis (1984)
{'key': 'e_1_2_3_58_2', 'volume-title': 'Modern Allene Chemistry', 'year': '2004'} / Modern Allene Chemistry (2004)
10.1021/ja046890q
An alternate explanation would imply that the reaction might not go through a discrete allene intermediate; hence a concerted mechanism would be worth consideration.
10.1002/ange.200501056
10.1002/anie.200501056

Dates

Type	When
Created	19 years, 4 months ago (April 26, 2006, 10:40 a.m.)
Deposited	1 year, 10 months ago (Oct. 16, 2023, 4:57 p.m.)
Indexed	1 month, 2 weeks ago (July 20, 2025, 12:19 a.m.)
Issued	19 years, 3 months ago (May 18, 2006)
Published	19 years, 3 months ago (May 18, 2006)
Published Online	19 years, 3 months ago (May 18, 2006)
Published Print	19 years, 3 months ago (May 26, 2006)

Funders 0

None

BibTeX

@article{Marion_2006, title={AuI‐Catalyzed Tandem [3,3] Rearrangement–Intramolecular Hydroarylation: Mild and Efficient Formation of Substituted Indenes}, volume={45}, ISSN={1521-3773}, url={http://dx.doi.org/10.1002/anie.200600571}, DOI={10.1002/anie.200600571}, number={22}, journal={Angewandte Chemie International Edition}, publisher={Wiley}, author={Marion, Nicolas and Díez‐González, Silvia and de Frémont, Pierre and Noble, April R. and Nolan, Steven P.}, year={2006}, month=may, pages={3647–3650} }

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