Literature DB >> 18754591

A sequential metal-catalyzed C-N bond formation in the synthesis of 2-amido-indoles.

Pei-Yuan Yao1, Yu Zhang, Richard P Hsung, Kang Zhao.   

Abstract

A sequential <span class="Chemical">metal-catalyzed C-N bond formation employing <class="Chemical">span class="Chemical">ortho-haloaryl acetylenic bromides is described. The initial amidation is highly selective for C (sp)-N bond formation, leading to o-haloaryl-substituted ynamides that can be useful building blocks, while the overall sequence provides a facile construction of 2-amido-indoles.

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Year:  2008        PMID: 18754591      PMCID: PMC2662137          DOI: 10.1021/ol801711p

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  51 in total

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4.  A copper-catalyzed C-N bond formation involving sp-hybridized carbons. A direct entry to chiral ynamides via N-alkynylation of amides.

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5.  Copper-catalyzed coupling of amides and carbamates with vinyl halides.

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6.  Expanding Pd-catalyzed C-N bond-forming processes: the first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions.

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8.  Copper-mediated synthesis of N-acyl vinylogous carbamic acids and derivatives: synthesis of the antibiotic CJ-15,801.

Authors:  Chong Han; Ruichao Shen; Shun Su; John A Porco
Journal:  Org Lett       Date:  2004-01-08       Impact factor: 6.005

9.  Copper-mediated N-alkynylation of carbamates, ureas, and sulfonamides. A general method for the synthesis of ynamides.

Authors:  Joshua R Dunetz; Rick L Danheiser
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10.  Modern synthetic methods for copper-mediated C(aryl)[bond]O, C(aryl)[bond]N, and C(aryl)[bond]S bond formation.

Authors:  Steven V Ley; Andrew W Thomas
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  8 in total

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Authors:  Kyle A DeKorver; Hongyan Li; Andrew G Lohse; Ryuji Hayashi; Zhenjie Lu; Yu Zhang; Richard P Hsung
Journal:  Chem Rev       Date:  2010-09-08       Impact factor: 60.622

2.  Synthesis of alpha-keto-imides via oxidation of ynamides.

Authors:  Ziyad F Al-Rashid; Whitney L Johnson; Richard P Hsung; Yonggang Wei; Pei-Yuan Yao; Renhei Liu; Kang Zhao
Journal:  J Org Chem       Date:  2008-10-21       Impact factor: 4.354

3.  Stereodefined trisubstituted enolates as a unique entry to all-carbon quaternary stereogenic centers in acyclic systems.

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4.  Synthesis of amidines using N-allyl ynamides. A palladium-catalyzed allyl transfer through an ynamido-pi-allyl complex.

Authors:  Yu Zhang; Kyle A DeKorver; Andrew G Lohse; Yan-Shi Zhang; Jian Huang; Richard P Hsung
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005

5.  A Rhodium(I)-Xylyl-BINAP Catalyzed Asymmetric Ynamide-[2 + 2 + 2] Cycloaddition in the Synthesis of Optically Enriched N,O-Biaryls.

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Journal:  Tetrahedron       Date:  2009-06-27       Impact factor: 2.457

6.  Synthesis of poly-functionalized benzofurans via one-pot domino oxidation/[3+2] cyclization reactions of a hydroquinone ester and ynamides.

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Journal:  RSC Adv       Date:  2019-04-25       Impact factor: 4.036

7.  Regio- and stereoselective carbometallation reactions of N-alkynylamides and sulfonamides.

Authors:  Yury Minko; Morgane Pasco; Helena Chechik; Ilan Marek
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8.  Palladium-catalyzed C-N and C-O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols.

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  8 in total

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