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Rhodium(I)-Catalyzed Synthesis of Indoles: Amino-Claisen Rearrangement of N-Propargylanilines
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Showa Pharmaceutical University.
, ‡Tokyo University of Pharmacy and Life Sciences.
Abstract
Mild and facile preparations of 2-substituted or 2,3-disubstituted indole compounds were achieved by RhH(CO)(Ph3P)3 (4−10 mol %)-catalyzed reaction of N-propargylanilines in hexafluoroisopropyl alcohol (HFIP). The formation of indoles was proven to be derived from an o-allenylaniline intermediate, which was generated by the Rh(I)-catalyzed amino-Claisen rearrangement of N-propargylanilines. The catalytic system is also available for the one-pot synthesis of indoles by reacting N-alkylaniline (1 equiv) with propargyl bromide (1.3 equiv) in the presence of K2CO3 (3 equiv) in HFIP. The active catalyst was proven to be [Rh(CO)(Ph3P)2]OCH(CF3)2 generated in situ from RhH(CO)(Ph3P)3 and HFIP. The structure of [Rh(CO)(Ph3P)2]OCH(CF3)2 was confirmed by single-crystal X-ray crystallographic analysis.
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This article has been cited by 4 ACS Journal articles (4 most recent appear below).
One-Pot Synthesis of 1,2-Dihydropyridines: Expanding the Diverse Reactivity of Propargyl Vinyl Ethers
Tobias Harschneck and Stefan F. KirschThe Journal of Organic Chemistry2011 76 (7), 2145-2156One-Pot Synthesis of 1,2-Dihydropyridines: Expanding the Diverse Reactivity of Propargyl Vinyl Ethers
Tobias Harschneck and Stefan F. KirschThe Journal of Organic Chemistry2011 76 (7), 2145-2156The catalyzed synthesis of 1,2-dihydropyridines starting from easily accessible propargyl vinyl ethers was realized. The reaction sequence involving a transition metal-catalyzed propargyl-Claisen rearrangement, a condensation step, and a Brønsted acid-...
Synthesis of Pyrroles by Gold(I)-Catalyzed Amino−Claisen Rearrangement of N-Propargyl Enaminone Derivatives
Akio Saito, Tomoyo Konishi and Yuji HanzawaOrganic Letters2010 12 (2), 372-374Synthesis of Pyrroles by Gold(I)-Catalyzed Amino−Claisen Rearrangement of N-Propargyl Enaminone Derivatives
Akio Saito, Tomoyo Konishi and Yuji HanzawaOrganic Letters2010 12 (2), 372-374The cationic N-heterocyclic carbene−gold(I) complex catalyzes the formation of tri- and tetrasubstituted pyrroles via the amino−Claisen rearrangement of N-propargyl β-enaminone derivatives and the cyclization of α-allenyl β-enaminone intermediates.
Cationic Rhodium(I)−dppf Complex-Catalyzed Olefin Isomerization/Propargyl Claisen Rearrangement/Carbonyl Migration Cascade
Ken Tanaka, Eri Okazaki and Yu ShibataJournal of the American Chemical Society2009 131 (31), 10822-10823Cationic Rhodium(I)−dppf Complex-Catalyzed Olefin Isomerization/Propargyl Claisen Rearrangement/Carbonyl Migration Cascade
Ken Tanaka, Eri Okazaki and Yu ShibataJournal of the American Chemical Society2009 131 (31), 10822-10823We have established that a cationic rhodium(I)−dppf complex catalyzes isomerizations of allyl propargyl ethers to allenic aldehydes in good yields from room temperature to 40 °C. On the other hand, carbonyl migration reactions from allenic aldehydes ...
Rhodium(I)-Catalyzed Synthesis of Indoles: Amino-Claisen Rearrangement of N-Propargylanilines
Akio Saito, Shoko Oda, Haruhiko Fukaya and Yuji HanzawaThe Journal of Organic Chemistry2009 74 (4), 1517-1524Rhodium(I)-Catalyzed Synthesis of Indoles: Amino-Claisen Rearrangement of N-Propargylanilines
Akio Saito, Shoko Oda, Haruhiko Fukaya and Yuji HanzawaThe Journal of Organic Chemistry2009 74 (4), 1517-1524Mild and facile preparations of 2-substituted or 2,3-disubstituted indole compounds were achieved by RhH(CO)(Ph3P)3 (4−10 mol %)-catalyzed reaction of N-propargylanilines in hexafluoroisopropyl alcohol (HFIP). The formation of indoles was proven to be ...
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History
- Published In Issue February 20, 2009
- Article ASAPJanuary 21, 2009
- Received: October 10, 2008
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