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Literature DB >> 26846436

Catalytic insertion of aldehydes into dihalonitroacetophenones via sequential bond scission-aldol reaction-acyl transfer.

Abstract

A catalytic process that provides dihalogenated nitro alcohols in up to 99% yield and with 100% atom economy is described. In situ cleavage of dihalonitroacetophenones affords nitronates that undergo Lewis acid catalyzed addition to aldehydes. Final benzoylation renders the sequence irreversible and regenerates the bond scission and acyl transfer agent.

Entities: Chemical

Mesh：

Substances：
Acetophenones
Aldehydes

Year: 2016 PMID： 26846436 PMCID： PMC4760845 DOI： 10.1039/c5cc09753c

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

27 in total

1. Asymmetric Alkylation of Nitroalkanes We thank the National Science Foundation and the National Institutes of Health (NIH), General Medical Sciences, for their generous support of our programs. Rhône-Poulenc graciously provided a postdoctoral fellowship for J.-P. S. Mass spectra were provided by the Mass Spectrometry Facility of the University of California, San Francisco, supported by the NIH Division of Research Resources.

Authors:
Journal: Angew Chem Int Ed Engl Date: 2000-09-01 Impact factor: 15.336

2. Recent Progress toward the Introduction of Functionalized Difluoromethylated Building Blocks onto C(sp(2) ) and C(sp) Centers.

Authors: Marie-Charlotte Belhomme; Tatiana Besset; Thomas Poisson; Xavier Pannecoucke
Journal: Chemistry Date: 2015-07-14 Impact factor: 5.236

3. Synthesis of undecachlorosulfolipid A: re-evaluation of the nominal structure.

Authors: Christian Nilewski; Nicholas R Deprez; Thomas C Fessard; Dong Bo Li; Roger W Geisser; Erick M Carreira
Journal: Angew Chem Int Ed Engl Date: 2011-07-08 Impact factor: 15.336

Review 4. Catalytic, asymmetric halofunctionalization of alkenes--a critical perspective.

Authors: Scott E Denmark; William E Kuester; Matthew T Burk
Journal: Angew Chem Int Ed Engl Date: 2012-09-25 Impact factor: 15.336

5. Enantioselective dichlorination of allylic alcohols.

Authors: K C Nicolaou; Nicholas L Simmons; Yongcheng Ying; Philipp M Heretsch; Jason S Chen
Journal: J Am Chem Soc Date: 2011-05-10 Impact factor: 15.419

6. Benzylation of nitroalkanes using copper-catalyzed thermal redox catalysis: toward the facile C-alkylation of nitroalkanes.

Authors: Peter G Gildner; Amber A S Gietter; Di Cui; Donald A Watson
Journal: J Am Chem Soc Date: 2012-06-12 Impact factor: 15.419

7. Total synthesis of a chlorosulpholipid cytotoxin associated with seafood poisoning.

Authors: Christian Nilewski; Roger W Geisser; Erick M Carreira
Journal: Nature Date: 2009-01-29 Impact factor: 49.962

Review 8. Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).

Authors: Jiang Wang; María Sánchez-Roselló; José Luis Aceña; Carlos del Pozo; Alexander E Sorochinsky; Santos Fustero; Vadim A Soloshonok; Hong Liu
Journal: Chem Rev Date: 2013-12-03 Impact factor: 60.622

9. Copper-mediated difluoromethylation of (hetero)aryl iodides and β-styryl halides with tributyl(difluoromethyl)stannane.

Authors: G K Surya Prakash; Somesh K Ganesh; John-Paul Jones; Aditya Kulkarni; Kamil Masood; Joseph K Swabeck; George A Olah
Journal: Angew Chem Int Ed Engl Date: 2012-10-25 Impact factor: 15.336

Catalytic insertion of aldehydes into dihalonitroacetophenones via sequential bond scission-aldol reaction-acyl transfer.

2. Recent Progress toward the Introduction of Functionalized Difluoromethylated Building Blocks onto C(sp(2) ) and C(sp) Centers.

3. Synthesis of undecachlorosulfolipid A: re-evaluation of the nominal structure.

Review 4. Catalytic, asymmetric halofunctionalization of alkenes--a critical perspective.

5. Enantioselective dichlorination of allylic alcohols.

6. Benzylation of nitroalkanes using copper-catalyzed thermal redox catalysis: toward the facile C-alkylation of nitroalkanes.

7. Total synthesis of a chlorosulpholipid cytotoxin associated with seafood poisoning.

Review 8. Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).

9. Copper-mediated difluoromethylation of (hetero)aryl iodides and β-styryl halides with tributyl(difluoromethyl)stannane.

10. Enantioselective total synthesis of (-)-napyradiomycin A1 via asymmetric chlorination of an isolated olefin.

1. Organocatalytic Stereoselective Synthesis of Fluorinated 3,3'-Linked Bisoxindoles.

2. Organocatalytic Insertion of Isatins into Aryl Difluoronitromethyl Ketones.

3. Enantioseparation and racemization of α-aryl-α-fluoroacetonitriles.

4. Palladium and Nickel Catalyzed Suzuki Cross-Coupling with Alkyl Fluorides.