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Literature DB >> 29641190

Ir(III)-Catalyzed Carbocarbation of Alkynes through Undirected Double C-H Bond Activation of Anisoles.

Fedor Romanov-Michailidis¹, Benjamin D Ravetz¹, Daniel W Paley^1,2, Tomislav Rovis¹.

Abstract

A novel, electron-deficient cyclopentadienyl iridium(III) catalyst enables sequential cleavage of arene C(sp2)-H and methoxy C(sp3)-H bonds of anisoles, generating reactive metalacycles that insert difluoroalkynes to afford chromenes under mild reaction conditions. This transformation is an arylalkylation of an alkyne-a carbocarbation-via a nonchelate-assisted cleavage of two C-H bonds.

Entities: Chemical Disease Species

Mesh：

Substances：

Year: 2018 PMID： 29641190 PMCID： PMC5972829 DOI： 10.1021/jacs.8b02716

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

23 in total

Review 1. Coumarins in polymers: from light harvesting to photo-cross-linkable tissue scaffolds.

Authors: Scott R Trenor; Allan R Shultz; Brian J Love; Timothy E Long
Journal: Chem Rev Date: 2004-06 Impact factor: 60.622

2. 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

3. A palladium-catalyzed oxidative cycloaromatization of biaryls with alkynes using molecular oxygen as the oxidant.

Authors: Zhuangzhi Shi; Shengtao Ding; Yuxin Cui; Ning Jiao
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

4. Substrate activation strategies in rhodium(III)-catalyzed selective functionalization of arenes.

Authors: Guoyong Song; Xingwei Li
Journal: Acc Chem Res Date: 2015-04-06 Impact factor: 22.384

5. Palladium-Catalyzed Transformations of Alkyl C-H Bonds.

Authors: Jian He; Masayuki Wasa; Kelvin S L Chan; Qian Shao; Jin-Quan Yu
Journal: Chem Rev Date: 2016-12-02 Impact factor: 60.622

6. Computational Studies of Carboxylate-Assisted C-H Activation and Functionalization at Group 8-10 Transition Metal Centers.

Authors: David L Davies; Stuart A Macgregor; Claire L McMullin
Journal: Chem Rev Date: 2017-05-22 Impact factor: 60.622

7. Electronic effects in iridium C-H borylations: insights from unencumbered substrates and variation of boryl ligand substituents.

Authors: Britt A Vanchura; Sean M Preshlock; Philipp C Roosen; Venkata A Kallepalli; Richard J Staples; Robert E Maleczka; Daniel A Singleton; Milton R Smith
Journal: Chem Commun (Camb) Date: 2010-09-20 Impact factor: 6.222

Review 8. Synthetic approaches to monofluoroalkenes.

Authors: Grégory Landelle; Maxime Bergeron; Marc-Olivier Turcotte-Savard; Jean-François Paquin
Journal: Chem Soc Rev Date: 2011-03-11 Impact factor: 54.564

9. Functionalization of Csp3-H and Csp2-H bonds: synthesis of spiroindenes by enolate-directed ruthenium-catalyzed oxidative annulation of alkynes with 2-aryl-1,3-dicarbonyl compounds.

Authors: Suresh Reddy Chidipudi; Imtiaz Khan; Hon Wai Lam
Journal: Angew Chem Int Ed Engl Date: 2012-10-24 Impact factor: 15.336

Ir(III)-Catalyzed Carbocarbation of Alkynes through Undirected Double C-H Bond Activation of Anisoles.

Review 1. Coumarins in polymers: from light harvesting to photo-cross-linkable tissue scaffolds.

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

3. A palladium-catalyzed oxidative cycloaromatization of biaryls with alkynes using molecular oxygen as the oxidant.

4. Substrate activation strategies in rhodium(III)-catalyzed selective functionalization of arenes.

5. Palladium-Catalyzed Transformations of Alkyl C-H Bonds.

6. Computational Studies of Carboxylate-Assisted C-H Activation and Functionalization at Group 8-10 Transition Metal Centers.

7. Electronic effects in iridium C-H borylations: insights from unencumbered substrates and variation of boryl ligand substituents.

Review 8. Synthetic approaches to monofluoroalkenes.

9. Functionalization of Csp3-H and Csp2-H bonds: synthesis of spiroindenes by enolate-directed ruthenium-catalyzed oxidative annulation of alkynes with 2-aryl-1,3-dicarbonyl compounds.

10. Rhodium(III)-catalyzed dearomatizing (3 + 2) annulation of 2-alkenylphenols and alkynes.

1. Ligand Controlled Ir-Catalyzed Regiodivergent Oxyamination of Unactivated Alkenes.

Review 2. Transition-Metal-Catalyzed Annulations Involving the Activation of C(sp³ )-H Bonds.

Review 1. Coumarins in polymers: from light harvesting to photo-cross-linkable tissue scaffolds.

Review 8. Synthetic approaches to monofluoroalkenes.

Review 2. Transition-Metal-Catalyzed Annulations Involving the Activation of C(sp3 )-H Bonds.

Review 2. Transition-Metal-Catalyzed Annulations Involving the Activation of C(sp³ )-H Bonds.