Synthesis of fused indoles by sequential palladium-catalyzed Heck reaction and N-heteroannulation

Söderberg, Björn C.G.; Hubbard, Jeremiah W.; Rector, Stacey R.; O'Neil, Shannon N.

doi:10.1016/j.tet.2005.02.033

Cited by 50 publications

(8 citation statements)

References 29 publications

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“…(341)) [1442]. Palladium-catalyzed reductive N-heteroannulations of aromatic 2-nitro-1-alkene derivatives in the presence of carbon monoxide to afford indoles [1443,1444] was used in a synthesis of KDR kinase inhibitors [376]. …”

Section: Other Heterocyclizationsmentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

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Section: Other Heterocyclizationsmentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

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“…2.2). Applying electron-rich phosphine ligands, P(o-tol) 3 [44] and PMe 3 (entries 9 and 10), gave low to moderate yields for the formation of 109. Bidentate phosphine ligand 1,3-bis (diphenylphosphino)propane (dppp) 134 gave only 109 in 88 % isolated yield (entry 11).…”

Section: Regioselectivity In the Intramolecular Heck Reaction Of Sulfmentioning

confidence: 99%

Selectivity in the Synthesis of Cyclic Sulfonamides

Geoghegan¹

2014

Springer Theses

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The series "Springer Theses" brings together a selection of the very best Ph.D. theses from around the world and across the physical sciences. Nominated and endorsed by two recognized specialists, each published volume has been selected for its scientific excellence and the high impact of its contents for the pertinent field of research. For greater accessibility to non-specialists, the published versions include an extended introduction, as well as a foreword by the student's supervisor explaining the special relevance of the work for the field. As a whole, the series will provide a valuable resource both for newcomers to the research fields described, and for other scientists seeking detailed background information on special questions. Finally, it provides an accredited documentation of the valuable contributions made by today's younger generation of scientists.Theses are accepted into the series by invited nomination only and must fulfill all of the following criteria • They must be written in good English.• The topic should fall within the confines of Chemistry, Physics, Earth Sciences, Engineering and related interdisciplinary fields such as Materials, Nanoscience, Chemical Engineering, Complex Systems and Biophysics.

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“…Our previously published methodology 80 Subjecting compound 87 to these conditions did not give the expected indole or any other identifiable products (Table 7). Other heterocycles have been synthesized in our group using alternate conditions or palladium diacetate and 1,10-phenanthroline under a carbon monoxide atmosphere with good results.…”

Section: G Reductive N-heteroannulationmentioning

confidence: 94%

“…This combination has previously been employed successfully in the synthesis 3,4-fused indoles 80 , 1,2-dihydro-4(3H)-carbazolones 83 , and β-carbolines 84 . However, for the transformation of 8 to 30, a much higher yield was achieved using only 1,10phenanthroline as the ligand (Table 4, entry 2).…”

Section: E Natural Product Syntheses Of Ht-13-a and Ht-13-bmentioning

confidence: 99%

“…It is used to form the fused ring and to position the double bond for cyclization to the indole while not affecting the stereochemistry of the molecules (Scheme 24). Our previous methodology 80 to fused indoles demonstrated the feasibility of using the Heck reaction to form a seven member heterocyclic ring and leading into the Nheteroannulation to form the indole ring.…”

Section: F Intramolecular Heck Reactionmentioning

confidence: 99%

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Synthesis of substituted 2-vinyl and 2-phenylbenzimidazoles and progress towards the synthesis of natural products ht-13-A and ht-13-B

Hubbard¹

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Synthesis of 2-alkenyl and 2-arylbenzimidazoles, having a variety of functional groups, has been accomplished via a novel palladium-catalyzed reductive N-heteroannulation of 2-nitro-N-alkyl or N-benzyl benzenamines. The cyclization precursors are readily prepared from commercially available compounds by a variety of methods. In addition, the first total synthesis of ht-13-A has been studied. The key steps of the synthesis are a Mitsunobu reaction, an intramolecular Heck reaction, and a reductive Nheteroannulation.

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Synthesis of fused indoles by sequential palladium-catalyzed Heck reaction and N-heteroannulation

Cited by 50 publications

References 29 publications

Transition metals in organic synthesis: Highlights for the year 2005

Transition metals in organic synthesis: Highlights for the year 2005

Selectivity in the Synthesis of Cyclic Sulfonamides

Synthesis of substituted 2-vinyl and 2-phenylbenzimidazoles and progress towards the synthesis of natural products ht-13-A and ht-13-B

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