Through-Space 1,4-Palladium Migration and 1,2-Aryl Shift: Direct Access to Dibenzo[a,c]carbazoles through a Triple C¢H Functionalization Cascade
IR@IICB: CSIR-Indian Institute of Chemical Biology, Kolkata
View Archive Info| Field | Value | |
| Title |
Through-Space 1,4-Palladium Migration and 1,2-Aryl Shift: Direct Access to Dibenzo[a,c]carbazoles through a Triple C¢H
Functionalization Cascade
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| Creator |
Bhunia, Samir Kumar
Polley, Arghya Natarajan, Ramalingam Jana, Ranjan |
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| Subject |
Chemistry
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| Description |
A palladium-catalyzed expeditious synthesis of
dibenzofused carbazoles from readily available 2-arylindoles
and diaryliodonium salts is reported. Interestingly,
after the electrophilic C3 palladation of indole, an unexpected “through-space” 1,4-palladium migration to the 2-
aryl moiety, by remote C¢H bond activation followed by
C¢H arylation with diaryliodonium salt, and an unprecedented
1,2-aryl shift take place. Finally, an intramolecular
cross-dehydrogenative coupling (CDC) at the C2 position
affords dibenzo[a,c]carbazoles in high yields. Remarkably,
the present migratory annulation occurs through three C¢
H bond activation one C¢C bond cleavage, and the simultaneous construction of three new C¢C bonds in a single
operation.
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| Date |
2015
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| Type |
Article
PeerReviewed |
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| Format |
application/pdf
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| Identifier |
http://www.eprints.iicb.res.in/2452/1/CHEMISTRY%2DA_EUROPEAN_JOURNAL__Vol.__21(__47_)_16786%2D16791;2015.pdf
Bhunia, Samir Kumar and Polley, Arghya and Natarajan, Ramalingam and Jana, Ranjan (2015) Through-Space 1,4-Palladium Migration and 1,2-Aryl Shift: Direct Access to Dibenzo[a,c]carbazoles through a Triple C¢H Functionalization Cascade. Chemistry-A European Journal, 21 (47). pp. 16786-16791. |
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| Relation |
http://dx.doi.org/10.1002/chem.201503474
http://www.eprints.iicb.res.in/2452/ |
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