Domino or Single-Step Tsuji-Trost/Heck Reactions and Their Application in the Synthesis of 3-Benzazepines and Azepino[4,5-b]indole Ring Systems

Scott Stewart; Charles Heath; Emilio Ghisalberti

doi:10.1002/ejoc.200900028

Domino or Single-Step Tsuji-Trost/Heck Reactions and Their Application in the Synthesis of 3-Benzazepines and Azepino[4,5-b]indole Ring Systems

Scott Stewart, Charles Heath, Emilio Ghisalberti

School of Molecular Sciences

Research output: Contribution to journal › Article › peer-review

37 Citations (Scopus)

Abstract

A series of methods for palladium-mediated single-step and domino Tsuji–Trost/Heck reactions are described. These methods are applied to the synthesis of both 3-benzazepines and azepino[4,5-b]indoles in the category of complex 6-7-6 and 6-5-7 ring heterocycles. In addition, a domino Heck/Heck sequence of reactions that produces the azepinobenzindolizine tetracyclic ring system from N-diallylated precursors is described.

Original language	English
Pages (from-to)	1934-1943
Journal	European Journal of Organic Chemistry
Volume	2009
Issue number	12
DOIs	https://doi.org/10.1002/ejoc.200900028
Publication status	Published - 2009

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10.1002/ejoc.200900028

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abstract = "A series of methods for palladium-mediated single-step and domino Tsuji–Trost/Heck reactions are described. These methods are applied to the synthesis of both 3-benzazepines and azepino[4,5-b]indoles in the category of complex 6-7-6 and 6-5-7 ring heterocycles. In addition, a domino Heck/Heck sequence of reactions that produces the azepinobenzindolizine tetracyclic ring system from N-diallylated precursors is described.",

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AU - Heath, Charles

AU - Ghisalberti, Emilio

PY - 2009

Y1 - 2009

N2 - A series of methods for palladium-mediated single-step and domino Tsuji–Trost/Heck reactions are described. These methods are applied to the synthesis of both 3-benzazepines and azepino[4,5-b]indoles in the category of complex 6-7-6 and 6-5-7 ring heterocycles. In addition, a domino Heck/Heck sequence of reactions that produces the azepinobenzindolizine tetracyclic ring system from N-diallylated precursors is described.

AB - A series of methods for palladium-mediated single-step and domino Tsuji–Trost/Heck reactions are described. These methods are applied to the synthesis of both 3-benzazepines and azepino[4,5-b]indoles in the category of complex 6-7-6 and 6-5-7 ring heterocycles. In addition, a domino Heck/Heck sequence of reactions that produces the azepinobenzindolizine tetracyclic ring system from N-diallylated precursors is described.

U2 - 10.1002/ejoc.200900028

DO - 10.1002/ejoc.200900028

M3 - Article

SN - 1434-193X

VL - 2009

SP - 1934

EP - 1943

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 12

ER -

Domino or Single-Step Tsuji-Trost/Heck Reactions and Their Application in the Synthesis of 3-Benzazepines and Azepino[4,5-b]indole Ring Systems

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