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

Literature DB >> 19199763

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

Yu Zhang¹, Kyle A DeKorver, Andrew G Lohse, Yan-Shi Zhang, Jian Huang, Richard P Hsung.

Abstract

A de novo transformation of N-allyl-N-sulfonyl ynamides to amidines is described featuring a palladium-catalyzed N-to-C allyl transfer via ynamido-palladium-pi-allyl complexes.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2009 PMID： 19199763 PMCID： PMC2683379 DOI： 10.1021/ol802844z

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

43 in total

1. Click Chemistry: Diverse Chemical Function from a Few Good Reactions.

Authors: Hartmuth C. Kolb; M. G. Finn; K. Barry Sharpless
Journal: Angew Chem Int Ed Engl Date: 2001-06-01 Impact factor: 15.336

2. An efficient synthesis of bicyclic amidines by intramolecular cyclization.

Authors: Naoya Kumagai; Shigeki Matsunaga; Masakatsu Shibasaki
Journal: Angew Chem Int Ed Engl Date: 2004-01-16 Impact factor: 15.336

3. Efficiency and fidelity in a click-chemistry route to triazole dendrimers by the copper(i)-catalyzed ligation of azides and alkynes.

Authors: Peng Wu; Alina K Feldman; Anne K Nugent; Craig J Hawker; Arnulf Scheel; Brigitte Voit; Jeffrey Pyun; Jean M J Fréchet; K Barry Sharpless; Valery V Fokin
Journal: Angew Chem Int Ed Engl Date: 2004-07-26 Impact factor: 15.336

4. Efficient microwave access to polysubstituted amidines from imidoylbenzotriazoles.

Authors: Alan R Katritzky; Chunming Cai; Sandeep K Singh
Journal: J Org Chem Date: 2006-04-28 Impact factor: 4.354

5. Highly efficient one-pot synthesis of N-sulfonylamidines by Cu-catalyzed three-component coupling of sulfonyl azide, alkyne, and amine.

Authors: Imhyuck Bae; Hoon Han; Sukbok Chang
Journal: J Am Chem Soc Date: 2005-02-23 Impact factor: 15.419

6. A facile access to N-sulfonylimidates and their synthetic utility for the transformation to amidines and amides.

Authors: Eun Jeong Yoo; Imhyuck Bae; Seung Hwan Cho; Hoon Han; Sukbok Chang
Journal: Org Lett Date: 2006-03-30 Impact factor: 6.005

7. Copper-catalyzed hydrative amide synthesis with terminal alkyne, sulfonyl azide, and water.

Authors: Seung Hwan Cho; Eun Jeong Yoo; Imhyuck Bae; Sukbok Chang
Journal: J Am Chem Soc Date: 2005-11-23 Impact factor: 15.419

8. Practical synthesis of amides from in situ generated copper(I) acetylides and sulfonyl azides.

Authors: Michael P Cassidy; Jessica Raushel; Valery V Fokin
Journal: Angew Chem Int Ed Engl Date: 2006-05-05 Impact factor: 15.336

9. Organic azides: an exploding diversity of a unique class of compounds.

Authors: Stefan Bräse; Carmen Gil; Kerstin Knepper; Viktor Zimmermann
Journal: Angew Chem Int Ed Engl Date: 2005-08-19 Impact factor: 15.336

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

Authors: Xiaohua Huang; Kevin W Anderson; Danilo Zim; Lei Jiang; Artis Klapars; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2003-06-04 Impact factor: 15.419

15 in total

1. An intramolecular [2 + 2] cycloaddition of ketenimines via palladium-catalyzed rearrangements of N-allyl-ynamides.

Authors: Kyle A DeKorver; Richard P Hsung; Wang-Ze Song; Xiao-Na Wang; Mary C Walton
Journal: Org Lett Date: 2012-06-05 Impact factor: 6.005

2. An Efficient Synthesis of de novo Imidates via Aza-Claisen Rearrangements of N-Allyl Ynamides.

Authors: Kyle A Dekorver; Troy D North; Richard P Hsung
Journal: Synlett Date: 2010-10 Impact factor: 2.454

Review 3. Ynamides: a modern functional group for the new millennium.

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

4. A divergent mechanistic course of Pd(0)-catalyzed aza-Claisen rearrangement and aza-Rautenstrauch-type cyclization of N-allyl ynamides.

Authors: Kyle A Dekorver; Richard P Hsung; Andrew G Lohse; Yu Zhang
Journal: Org Lett Date: 2010-04-16 Impact factor: 6.005

5. N-allyl-N-sulfonyl ynamides as synthetic precursors to amidines and vinylogous amidines. An unexpected N-to-C 1,3-sulfonyl shift in nitrile synthesis.

Authors: Kyle A DeKorver; Whitney L Johnson; Yu Zhang; Richard P Hsung; Huifang Dai; Jun Deng; Andrew G Lohse; Yan-Shi Zhang
Journal: J Org Chem Date: 2011-05-24 Impact factor: 4.354

6. Lithium Hexamethyldisilazane Transformation of Transiently Protected 4-Aza/Benzimidazole Nitriles to Amidines and their Dimethyl Sulfoxide Mediated Imidazole Ring Formation.

Authors: Reham A I Abou-Elkhair; Abdalla E A Hassan; David W Boykin; W David Wilson
Journal: Org Lett Date: 2016-09-08 Impact factor: 6.005

7. Benzannulation via the reaction of ynamides and vinylketenes. application to the synthesis of highly substituted indoles.

Authors: Tin Yiu Lam; Yu-Pu Wang; Rick L Danheiser
Journal: J Org Chem Date: 2013-09-03 Impact factor: 4.354

8. Carbocyclization cascades of allyl ketenimines via aza-Claisen rearrangements of N-phosphoryl-N-allyl-ynamides.

Authors: Kyle A DeKorver; Xiao-Na Wang; Mary C Walton; Richard P Hsung
Journal: Org Lett Date: 2012-03-13 Impact factor: 6.005

9. Synthesis of cyclopentenimines from N-allyl ynamides via a tandem aza-Claisen rearrangement-carbocyclization sequence.

Authors: Xiao-Na Wang; Gabrielle N Winston-McPherson; Mary C Walton; Yu Zhang; Richard P Hsung; Kyle A DeKorver
Journal: J Org Chem Date: 2013-06-10 Impact factor: 4.354

10. Highly substituted 2-amido-furans from Rh(II)-catalyzed cyclopropenations of ynamides.

Authors: Hongyan Li; Richard P Hsung
Journal: Org Lett Date: 2009-10-01 Impact factor: 6.005