Literature DB >> 18837553

Stereoselective synthesis of 3-alkylideneoxindoles by palladium-catalyzed cyclization reaction of 2-(alkynyl)aryl isocyanates with organoboron reagents.

Tomoya Miura1, Takeharu Toyoshima, Yusuke Takahashi, Masahiro Murakami.   

Abstract

A palladium(0)/monophosphine catalyst promotes a cyclization reaction of 2-(alkynyl)aryl isocyanates with organoboron reagents to produce stereodefined 3-alkylideneoxindoles. The alkynyl and isocyanato groups undergo oxidative cyclization with Pd(0) to form an oxapalladacycle intermediate. Subsequent transmetalation and reductive elimination afford the product.

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Year:  2008        PMID: 18837553     DOI: 10.1021/ol801844w

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


  5 in total

1.  Synthesis of Benzofused O- and N-Heterocycles through Cascade Carbopalladation/Cross-Alkylation of Alkynes Involving the C-C Cleavage of Cyclobutanols.

Authors:  Marta Pérez-Gómez; Piedad Herrera-Ramírez; Delia Bautista; Isabel Saura-Llamas; José-Antonio García-López
Journal:  Organometallics       Date:  2022-03-03       Impact factor: 3.876

2.  E-Z isomerization of 3-benzylidene-indolin-2-ones using a microfluidic photo-reactor.

Authors:  Chada Raji Reddy; Veeramalla Ganesh; Ajay K Singh
Journal:  RSC Adv       Date:  2020-08-03       Impact factor: 4.036

3.  The transient-chelating-group-controlled stereoselective Rh(i)-catalyzed silylative aminocarbonylation of 2-alkynylanilines: access to (Z)-3-(silylmethylene)indolin-2-ones.

Authors:  Ya-Fei Han; Gui-Fen Lv; Yang Li; Li-Jun Wu; Xuan-Hui Ouyang; Jin-Heng Li
Journal:  Chem Sci       Date:  2022-07-27       Impact factor: 9.969

4.  Non-Palladium-Catalyzed Approach to the Synthesis of (E)-3-(1,3-Diarylallylidene)Oxindoles.

Authors:  Jahyun Koo; Minsu Kim; Kye Jung Shin; Jae Hong Seo
Journal:  Molecules       Date:  2022-08-19       Impact factor: 4.927

5.  Nickel-catalyzed cyclization of alkyne-nitriles with organoboronic acids involving anti-carbometalation of alkynes.

Authors:  Xingjie Zhang; Xin Xie; Yuanhong Liu
Journal:  Chem Sci       Date:  2016-05-19       Impact factor: 9.825

  5 in total

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