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Literature DB >> 27790910

Ti-Catalyzed Multicomponent Oxidative Carboamination of Alkynes with Alkenes and Diazenes.

Zachary W Davis-Gilbert¹, Letitia J Yao¹, Ian A Tonks¹.

Abstract

The inter- or intramolecular oxidative carboamination of alkynes catalyzed by [py2TiCl2NPh]2 is reported. These multicomponent reactions couple alkenes, alkynes and diazenes to form either α,β-unsaturated imines or α-(iminomethyl)cyclopropanes via a TiII/TiIV redox cycle. Each of these products is formed from a common azatitanacyclohexene intermediate that undergoes either β-H elimination or α,γ-coupling, wherein the selectivity is under substrate control.

Entities: Chemical Gene

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Year: 2016 PMID： 27790910 PMCID： PMC5496654 DOI： 10.1021/jacs.6b09939

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

18 in total

Review 1. Hydroamination: direct addition of amines to alkenes and alkynes.

Authors: Thomas E Müller; Kai C Hultzsch; Miguel Yus; Francisco Foubelo; Mizuki Tada
Journal: Chem Rev Date: 2008-08-26 Impact factor: 60.622

Review 2. Heterocycles from cyclopropanes: applications in natural product synthesis.

Authors: Cheryl A Carson; Michael A Kerr
Journal: Chem Soc Rev Date: 2009-07-10 Impact factor: 54.564

3. Titanium-catalyzed multicomponent couplings: efficient one-pot syntheses of nitrogen heterocycles.

Authors: Aaron L Odom; Tanner J McDaniel
Journal: Acc Chem Res Date: 2015-08-21 Impact factor: 22.384

4. Reactions of Imines with Azazirconacyclobutenes and Generation of Electron-Deficient Imidozirconocene Complexes.

Authors: Rebecca T Ruck; Robert G Bergman
Journal: Organometallics Date: 2004-05-10 Impact factor: 3.876

5. The tunable functionality of alpha,beta-unsaturated carbonyl compounds enables their differential application in biological systems.

Authors: Sabine Amslinger
Journal: ChemMedChem Date: 2010-03-01 Impact factor: 3.466

6. Rhodium-catalyzed transannulation of 1,2,3-triazoles with nitriles.

Authors: Tony Horneff; Stepan Chuprakov; Natalia Chernyak; Vladimir Gevorgyan; Valery V Fokin
Journal: J Am Chem Soc Date: 2008-10-15 Impact factor: 15.419

7. Mechanistic studies of olefin and alkyne trimerization with chromium catalysts: deuterium labeling and studies of regiochemistry using a model chromacyclopentane complex.

Authors: Theodor Agapie; Jay A Labinger; John E Bercaw
Journal: J Am Chem Soc Date: 2007-10-31 Impact factor: 15.419

8. Nickel-catalyzed decarboxylative carboamination of alkynes with isatoic anhydrides.

Authors: Yasufumi Yoshino; Takuya Kurahashi; Seijiro Matsubara
Journal: J Am Chem Soc Date: 2009-06-10 Impact factor: 15.419

9. Synthesis of substituted 2-aminoimidazoles via Pd-catalyzed alkyne carboamination reactions. Application to the synthesis of preclathridine natural products.

Authors: Blane P Zavesky; Nicholas R Babij; John P Wolfe
Journal: Org Lett Date: 2014-09-08 Impact factor: 6.005

10. Rhodium-catalysed syn-carboamination of alkenes via a transient directing group.

Authors: Tiffany Piou; Tomislav Rovis
Journal: Nature Date: 2015-10-21 Impact factor: 49.962

17 in total

1. Synthesis of Pyridylimido Complexes of Tantalum and Niobium by Reductive Cleavage of the N═N Bond of 2,2'-Azopyridine: Precursors for Early-Late Heterobimetallic Complexes.

Authors: Kento Kawakita; Yuya Kakiuchi; Evan P Beaumier; Ian A Tonks; Hayato Tsurugi; Kazushi Mashima
Journal: Inorg Chem Date: 2019-09-25 Impact factor: 5.165

2. Oxidative nitrene transfer from azides to alkynes via Ti(ii)/Ti(iv) redox catalysis: formal [2+2+1] synthesis of pyrroles.

Authors: Adam J Pearce; Xin Yi See; Ian A Tonks
Journal: Chem Commun (Camb) Date: 2018-06-19 Impact factor: 6.222

3. Catalytic Alkyne Arylation Using Traceless Directing Groups.

Authors: Jung-Woo Park; Bubwoong Kang; Vy M Dong
Journal: Angew Chem Int Ed Engl Date: 2018-09-11 Impact factor: 15.336

4. Group 4 Diarylmetallocenes as Bespoke Aryne Precursors for Titanium-Catalyzed [2 + 2 + 2] Cycloaddition of Arynes and Alkynes.

Authors: Benjamin R Reiner; Ian A Tonks
Journal: Inorg Chem Date: 2019-06-12 Impact factor: 5.165

5. Trimethylsilyl-Protected Alkynes as Selective Cross-Coupling Partners in Titanium-Catalyzed [2+2+1] Pyrrole Synthesis.

Authors: Hsin-Chun Chiu; Ian A Tonks
Journal: Angew Chem Int Ed Engl Date: 2018-04-25 Impact factor: 15.336

6. Generation of Ti^II Alkyne Trimerization Catalysts in the Absence of Strong Metal Reductants.

Authors: Xin Yi See; Evan P Beaumier; Zachary W Davis-Gilbert; Peter L Dunn; Jacob A Larsen; Adam J Pearce; T Alex Wheeler; Ian A Tonks
Journal: Organometallics Date: 2017-03-29 Impact factor: 3.876

7. In Situ Catalyst Generation and Benchtop-Compatible Entry Points for Ti^II/Ti^IV Redox Catalytic Reactions.

Authors: Zachary W Davis-Gilbert; Kento Kawakita; Daniel R Blechschmidt; Hayato Tsurugi; Kazushi Mashima; Ian A Tonks
Journal: Organometallics Date: 2018-09-06 Impact factor: 3.876

8. Nickel-Catalyzed Dearomative trans-1,2-Carboamination.

Authors: Lucas W Hernandez; Ulrich Klöckner; Jola Pospech; Lilian Hauss; David Sarlah
Journal: J Am Chem Soc Date: 2018-03-23 Impact factor: 15.419

9. Reactivity of terminal imido complexes of group 4-6 metals: stoichiometric and catalytic reactions involving cycloaddition with unsaturated organic molecules.

Authors: Kento Kawakita; Yuya Kakiuchi; Hayato Tsurugi; Kazushi Mashima; Bernard F Parker; John Arnold; Ian A Tonks
Journal: Coord Chem Rev Date: 2020-01-14 Impact factor: 22.315

10. Mechanism of Ti-Catalyzed Oxidative Nitrene Transfer in [2 + 2 + 1] Pyrrole Synthesis from Alkynes and Azobenzene.

Authors: Zachary W Davis-Gilbert; Xuelan Wen; Jason D Goodpaster; Ian A Tonks
Journal: J Am Chem Soc Date: 2018-05-31 Impact factor: 15.419