Literature DB >> 29988985

Rhodium(III)-catalyzed C-H functionalization of C-alkenyl azoles with sulfoxonium ylides for the synthesis of bridgehead N-fused [5,6]-bicyclic heterocycles.

Gia L Hoang1, Jonathan A Ellman1.   

Abstract

The synthesis of bridgehead N-fused [5,6]-bicyclic heterocycles via rhodium(III)-catalyzed C-H functionalization of C-alkenyl azoles with sulfoxonium ylides is disclosed. Reactions proceeded in good to high yields for a range of aryl, heteroaryl and alkyl sulfoxonium ylides. In addition, 2-alkenyl imidazoles with different substitution patterns as well as C-alkenyl triazoles were effective inputs. The reaction could also be performed under straightforward bench top conditions.

Entities:  

Keywords:  Catalysis; C–H functionalization; Nitrogen heterocycle; Rhodium; Sulfoxonium ylide

Year:  2018        PMID: 29988985      PMCID: PMC6034689          DOI: 10.1016/j.tet.2018.03.062

Source DB:  PubMed          Journal:  Tetrahedron        ISSN: 0040-4020            Impact factor:   2.457


  26 in total

1.  Oxidative coupling of aromatic substrates with alkynes and alkenes under rhodium catalysis.

Authors:  Tetsuya Satoh; Masahiro Miura
Journal:  Chemistry       Date:  2010-10-04       Impact factor: 5.236

2.  Combined experimental and computational investigations of rhodium- and ruthenium-catalyzed C-H functionalization of pyrazoles with alkynes.

Authors:  Andrés G Algarra; Warren B Cross; David L Davies; Qudsia Khamker; Stuart A Macgregor; Claire L McMullin; Kuldip Singh
Journal:  J Org Chem       Date:  2014-02-24       Impact factor: 4.354

3.  Rhodium(III)-catalyzed oxidative coupling of 5-aryl-1H-pyrazoles with alkynes and acrylates.

Authors:  Xingwei Li; Miao Zhao
Journal:  J Org Chem       Date:  2011-09-26       Impact factor: 4.354

4.  Ruthenium-catalyzed alkyne annulations with substituted 1H-pyrazoles by C-H/N-H bond functionalizations.

Authors:  Wenbo Ma; Karolina Graczyk; Lutz Ackermann
Journal:  Org Lett       Date:  2012-12-12       Impact factor: 6.005

5.  Synthesis of [5,6]-Bicyclic Heterocycles with a Ring-Junction Nitrogen Atom: Rhodium(III)-Catalyzed C-H Functionalization of Alkenyl Azoles.

Authors:  Kim Søholm Halskov; Howard S Roth; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-05       Impact factor: 15.336

6.  Sulfoxonium Ylides as a Carbene Precursor in Rh(III)-Catalyzed C-H Acylmethylation of Arenes.

Authors:  Youwei Xu; Xukai Zhou; Guangfan Zheng; Xingwei Li
Journal:  Org Lett       Date:  2017-09-13       Impact factor: 6.005

Review 7.  C-H bond functionalization: emerging synthetic tools for natural products and pharmaceuticals.

Authors:  Junichiro Yamaguchi; Atsushi D Yamaguchi; Kenichiro Itami
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-06       Impact factor: 15.336

8.  Iridium-catalyzed X-H insertions of sulfoxonium ylides.

Authors:  Ian K Mangion; Ikenna K Nwamba; Michael Shevlin; Mark A Huffman
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005

9.  Fluorescent naphthyl- and anthrylazoles from the catalytic coupling of phenylazoles with internal alkynes through the cleavage of multiple C-H bonds.

Authors:  Nobuyoshi Umeda; Hayato Tsurugi; Tetsuya Satoh; Masahiro Miura
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

10.  One-carbon chain extension of esters to alpha-chloroketones: a safer route without diazomethane.

Authors:  Dengjin Wang; Mark D Schwinden; Lilian Radesca; Bharat Patel; David Kronenthal; Ming-Hsing Huang; William A Nugent
Journal:  J Org Chem       Date:  2004-03-05       Impact factor: 4.354

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  4 in total

1.  Three-Component Coupling of Aldehydes, Aminopyrazoles, and Sulfoxonium Ylides via Rhodium(III)-Catalyzed Imidoyl C-H Activation: Synthesis of Pyrazolo[1,5- a]pyrimidines.

Authors:  Gia L Hoang; Andrew D Streit; Jonathan A Ellman
Journal:  J Org Chem       Date:  2018-12-10       Impact factor: 4.354

2.  A Catalytic Cross-Olefination of Diazo Compounds with Sulfoxonium Ylides.

Authors:  James D Neuhaus; Adriano Bauer; Alexandre Pinto; Nuno Maulide
Journal:  Angew Chem Int Ed Engl       Date:  2018-11-08       Impact factor: 15.336

3.  Chemospecific Cyclizations of α-Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls.

Authors:  Daniel Clare; Benjamin C Dobson; Phillip A Inglesby; Christophe Aïssa
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-24       Impact factor: 15.336

4.  Ruthenium(II)-Catalyzed Homocoupling of α-Carbonyl Sulfoxonium Ylides Under Mild Conditions: Methodology Development and Mechanistic DFT Study.

Authors:  Maosheng Zhang; Jinrong Zhang; Zhenfang Teng; Jianhui Chen; Yuanzhi Xia
Journal:  Front Chem       Date:  2020-09-16       Impact factor: 5.221

  4 in total

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