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Literature DB >> 19277394

Highly efficient synthesis of aldenamines from carboxamides by iridium-catalyzed silane-reduction/dehydration under mild conditions.

Yukihiro Motoyama¹, Masaharu Aoki, Naoki Takaoka, Ryuta Aoto, Hideo Nagashima.

Abstract

The combination of IrCl(CO)(PPh3)2 with 1,1,3,3-tetramethyldisiloxane or poly(methylhydrosiloxane) (PMHS) is found to be an efficient catalyst system for the preparation of aldenamines from carboxamides; in particular, facile removal of silicone and iridium residues from the product can be achieved by the use of PMHS.

Entities: Chemical Disease Gene

Year: 2009 PMID： 19277394 DOI： 10.1039/b821317h

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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Cited

8 in total

1. CuH-Catalyzed Asymmetric Reductive Amidation of α,β-Unsaturated Carboxylic Acids.

Authors: Achim Link; Yujing Zhou; Stephen L Buchwald
Journal: Org Lett Date: 2020-07-06 Impact factor: 6.005

2. Site-Selective and Stereoselective trans-Hydroboration of 1,3-Enynes Catalyzed by 1,4-Azaborine-Based Phosphine-Pd Complex.

Authors: Senmiao Xu; Yuanzhe Zhang; Bo Li; Shih-Yuan Liu
Journal: J Am Chem Soc Date: 2016-11-01 Impact factor: 15.419

8. A General Iridium-Catalyzed Reductive Dienamine Synthesis Allows a Five-Step Synthesis of Catharanthine via the Elusive Dehydrosecodine.

Authors: Pablo Gabriel; Yaseen A Almehmadi; Zeng Rong Wong; Darren J Dixon
Journal: J Am Chem Soc Date: 2021-07-13 Impact factor: 15.419

8 in total

Highly efficient synthesis of aldenamines from carboxamides by iridium-catalyzed silane-reduction/dehydration under mild conditions.

1. CuH-Catalyzed Asymmetric Reductive Amidation of α,β-Unsaturated Carboxylic Acids.

2. Site-Selective and Stereoselective trans-Hydroboration of 1,3-Enynes Catalyzed by 1,4-Azaborine-Based Phosphine-Pd Complex.

3. Iridium-catalyzed reductive nitro-Mannich cyclization.

4. Mild Reductive Functionalization of Amides into N-Sulfonylformamidines.

5. Tertiary amine synthesis via reductive coupling of amides with Grignard reagents.

6. Iridium-catalyzed reductive Ugi-type reactions of tertiary amides.

7. Direct synthesis of anomeric tetrazolyl iminosugars from sugar-derived lactams.

8. A General Iridium-Catalyzed Reductive Dienamine Synthesis Allows a Five-Step Synthesis of Catharanthine via the Elusive Dehydrosecodine.