Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Palladium-catalyzed direct C-h arylation of N-iminopyridinium ylides: application to the synthesis of (+/-)-anabasine.

Literature DB >> 18067305

Palladium-catalyzed direct C-h arylation of N-iminopyridinium ylides: application to the synthesis of (+/-)-anabasine.

Alexandre Larivée¹, James J Mousseau, André B Charette.

Abstract

Palladium-catalyzed direct C-H arylation of N-iminopyridinium ylides provides a powerful and versatile method for the synthesis of functionalized piperidines in good yields. Chemoselective functionalization of the pyridinium ring in the presence of a pyridine substituent is possible as exemplified by the expedient synthesis of anabasine in 61% overall yield over three steps.

Entities: Chemical

Mesh：

Substances：

Year: 2007 PMID： 18067305 DOI： 10.1021/ja710073n

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

Keyword Cloud
Cited

16 in total

1. C-H arylation of pyridines: high regioselectivity as a consequence of the electronic character of C-H bonds and heteroarene ring.

Authors: Pengfei Guo; Jung Min Joo; Souvik Rakshit; Dalibor Sames
Journal: J Am Chem Soc Date: 2011-09-22 Impact factor: 15.419

Review 10. Developing ligands for palladium(II)-catalyzed C-H functionalization: intimate dialogue between ligand and substrate.

Authors: Keary M Engle; Jin-Quan Yu
Journal: J Org Chem Date: 2013-05-03 Impact factor: 4.354

Palladium-catalyzed direct C-h arylation of N-iminopyridinium ylides: application to the synthesis of (+/-)-anabasine.

1. C-H arylation of pyridines: high regioselectivity as a consequence of the electronic character of C-H bonds and heteroarene ring.

2. Rh(I)-catalyzed direct arylation of azines.

3. Synthesis and Utility of Dihydropyridine Boronic Esters.

4. Pd0/PR3-catalyzed arylation of nicotinic and isonicotinic acid derivatives.

5. Rh(I)-catalyzed direct arylation of pyridines and quinolines.

6. Chichibabin-type direct alkylation of pyridyl alcohols with alkyl lithium reagents.

7. Carbon-hydrogen bond functionalization approach for the synthesis of fluorenones and ortho-arylated benzonitriles.

Review 8. Rhodium-catalyzed C-C bond formation via heteroatom-directed C-H bond activation.

9. Recent Advances in the C-H-Functionalization of the Distal Positions in Pyridines and Quinolines.

Review 10. Developing ligands for palladium(II)-catalyzed C-H functionalization: intimate dialogue between ligand and substrate.