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 Cobalt-Catalyzed, Aminoquinoline-Directed Functionalization of Phosphinic Amide sp2 C-H Bonds.

Literature DB >> 27525171

Cobalt-Catalyzed, Aminoquinoline-Directed Functionalization of Phosphinic Amide sp² C-H Bonds.

Tung Thanh Nguyen¹, Liene Grigorjeva¹, Olafs Daugulis¹.

Abstract

In this paper, we introduce arylphosphinic acid aminoquinoline amides as competent substrates for cobalt-catalyzed sp2 C-H bond functionalization. Specifically, the feasibility of their coupling with alkynes, alkenes, and allyl pivalate has been demonstrated. Reactions are catalyzed by simple Co(NO3)2 hydrate in ethanol or mixed dioxane/tBuOH solvent in the presence of Mn(OAc)3·2H2O additive, sodium pivalate, or acetate base and use oxygen from the air as an oxidant. Directing group removal affords ortho-functionalized P,P-diarylphosphinic acids.

Entities: Chemical Disease Gene

Keywords: C–H functionalization; alkenes; alkynes; cobalt; phosphinic amides

Year: 2015 PMID： 27525171 PMCID： PMC4980089 DOI： 10.1021/acscatal.5b02391

Source DB: PubMed Journal: ACS Catal Impact factor: 13.084

51 in total

1. Ru-, Rh-, and Pd-catalyzed C-C bond formation involving C-H activation and addition on unsaturated substrates: reactions and mechanistic aspects.

Authors: Vincent Ritleng; Claude Sirlin; Michel Pfeffer
Journal: Chem Rev Date: 2002-05 Impact factor: 60.622

2. Cobalt-catalyzed, room-temperature addition of aromatic imines to alkynes via directed C-H bond activation.

Authors: Pin-Sheng Lee; Takeshi Fujita; Naohiko Yoshikai
Journal: J Am Chem Soc Date: 2011-10-11 Impact factor: 15.419

3. Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

Authors: Dmitry Shabashov; Olafs Daugulis
Journal: J Am Chem Soc Date: 2010-03-24 Impact factor: 15.419

4. Pd-catalyzed cascade carbopalladation-annulation reaction of 3-(2-iodobenzyl)-indoles into fused 6/5/7/6- and 6/5/5/6- heterocyclic systems.

Authors: Natalia Chernyak; David Tilly; Zhou Li; Vladimir Gevorgyan
Journal: Chem Commun (Camb) Date: 2009-11-17 Impact factor: 6.222

Cobalt-Catalyzed, Aminoquinoline-Directed Functionalization of Phosphinic Amide sp² C-H Bonds.

1. Ru-, Rh-, and Pd-catalyzed C-C bond formation involving C-H activation and addition on unsaturated substrates: reactions and mechanistic aspects.

2. Cobalt-catalyzed, room-temperature addition of aromatic imines to alkynes via directed C-H bond activation.

3. Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

4. Pd-catalyzed cascade carbopalladation-annulation reaction of 3-(2-iodobenzyl)-indoles into fused 6/5/7/6- and 6/5/5/6- heterocyclic systems.

5. Chiral Cyclopentadienyls: Enabling Ligands for Asymmetric Rh(III)-Catalyzed C-H Functionalizations.

6. Cobalt-catalyzed C-H cyanation of (hetero)arenes and 6-arylpurines with N-cyanosuccinimide as a new cyanating agent.

7. Low-valent cobalt catalysis: new opportunities for C-H functionalization.

8. Mn-catalyzed aromatic C-H alkenylation with terminal alkynes.

9. Rhodium(III)-catalyzed oxidative coupling through C-H bond cleavage directed by phosphinoxy groups.

10. Cobalt-catalyzed C-H arylations, benzylations, and alkylations with organic electrophiles and beyond.

1. Aminoquinoline-directed, cobalt-catalyzed carbonylation of sulfonamide sp² C-H bonds.

2. Highly Stereoselective Cobalt(III)-Catalyzed Three-Component C-H Bond Addition Cascade.

3. Palladium-catalyzed, aminoquinoline-directed arylation of phosphonamidate and phosphinic amide sp³ C-H bonds.

4. Tailored trisubstituted chiral Cp ^x Rh^III catalysts for kinetic resolutions of phosphinic amides.

5. Cobalt-catalyzed annulation of styrenes with α-bromoacetic acids.

6. Cobalt-catalyzed electrooxidative C-H/N-H [4+2] annulation with ethylene or ethyne.

7. Mechanistic details of the cobalt-mediated dehydrogenative dimerization of aminoquinoline-directed benzamides.