Lithioarene Cycliacylation and Pd-Catalyzed Aminoethylation/Cyclization to Access Electronically Diverse Saturated Isoquinoline Derivatives

We report operationally facile methods for the synthesis of substituted dihydroisoquinolinones and tetrahydroisoquinolines from readily accessible o-bromobenzyl bromides and o-bromobenzaldehydes, respectively. While classical electrophilic aromatic substitution reactions are tailored to the construc...

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Veröffentlicht in:	Journal of organic chemistry 2022-01, Vol.87 (1), p.776-789
Hauptverfasser:	Buchman, Marek, Farney, Elliot P, Greszler, Stephen N, Altenbach, Robert J, Gfesser, Gregory A, Voight, Eric A
Format:	Artikel
Sprache:	eng
Schlagworte:	Catalysis Cyclization Isoquinolines Palladium Tetrahydroisoquinolines
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container_title	Journal of organic chemistry
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creator	Buchman, Marek Farney, Elliot P Greszler, Stephen N Altenbach, Robert J Gfesser, Gregory A Voight, Eric A
description	We report operationally facile methods for the synthesis of substituted dihydroisoquinolinones and tetrahydroisoquinolines from readily accessible o-bromobenzyl bromides and o-bromobenzaldehydes, respectively. While classical electrophilic aromatic substitution reactions are tailored to the construction of saturated isoquinolines derived from electron-rich precursors, we demonstrate efficient syntheses from electronically diverse substrates to produce cyclized products as single regioisomers.
doi_str_mv	10.1021/acs.joc.1c02302
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Org. Chem</addtitle><date>2022-01-07</date><risdate>2022</risdate><volume>87</volume><issue>1</issue><spage>776</spage><epage>789</epage><pages>776-789</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>We report operationally facile methods for the synthesis of substituted dihydroisoquinolinones and tetrahydroisoquinolines from readily accessible o-bromobenzyl bromides and o-bromobenzaldehydes, respectively. 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subjects	Catalysis Cyclization Isoquinolines Palladium Tetrahydroisoquinolines
title	Lithioarene Cycliacylation and Pd-Catalyzed Aminoethylation/Cyclization to Access Electronically Diverse Saturated Isoquinoline Derivatives
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