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Literature DB >> 23095043

Selective cross-coupling of organic halides with allylic acetates.

Lukiana L Anka-Lufford¹, Michael R Prinsell, Daniel J Weix.

Abstract

A general protocol for the coupling of haloarenes with a variety of n class="Chemical">allylic acetates is presented. Strengths of the method are a tolerance for electrophilic (ketone, aldehyde) and acidic (sulfonamide, trifluoroacetamide) substrates and the ability to couple with a variety of substituted allylic acetates. Secondary alkyl bromides can also be allylated under slightly modified conditions, demonstrating the generality of the approach. Finally, the coupling of a reactive vinyl halide could be achieved by the use of a very hindered ligand and more reactive, branched allylic acetates.

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Year: 2012 PMID： 23095043 PMCID： PMC3510762 DOI： 10.1021/jo302086g

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

44 in total

1. Rhodium-catalyzed cross-coupling of allyl alcohols with aryl- and vinylboronic acids in ionic liquids.

Authors: George W Kabalka; Gang Dong; Bollu Venkataiah
Journal: Org Lett Date: 2003-03-20 Impact factor: 6.005

2. Palladium-catalyzed alkylation-hydride reduction sequence: synthesis of meta-substituted arenes.

Authors: Thorsten Wilhelm; Mark Lautens
Journal: Org Lett Date: 2005-09-01 Impact factor: 6.005

3. Nickel-Catalyzed Direct Electrochemical Cross-Coupling between Aryl Halides and Activated Alkyl Halides.

Authors: Muriel Durandetti; Jean-Yves Nédélec; Jacques Périchon
Journal: J Org Chem Date: 1996-03-08 Impact factor: 4.354

4. Chemistry of organomanganese(II) compounds.

Authors: Gérard Cahiez; Christophe Duplais; Julien Buendia
Journal: Chem Rev Date: 2009-03-11 Impact factor: 60.622

5. Discovery of 4-[4-({(3R)-1-butyl-3-[(R)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undec-9-yl}methyl)phenoxy]benzoic acid hydrochloride: a highly potent orally available CCR5 selective antagonist.

Authors: Rena Nishizawa; Toshihiko Nishiyama; Katsuya Hisaichi; Chiaki Minamoto; Masayuki Murota; Yoshikazu Takaoka; Hisao Nakai; Hideaki Tada; Kenji Sagawa; Shiro Shibayama; Daikichi Fukushima; Kenji Maeda; Hiroaki Mitsuya
Journal: Bioorg Med Chem Date: 2011-05-20 Impact factor: 3.641

6. Cobalt-catalyzed reductive allylation of alkyl halides with allylic acetates or carbonates.

Authors: Xin Qian; Audrey Auffrant; Abdellah Felouat; Corinne Gosmini
Journal: Angew Chem Int Ed Engl Date: 2011-09-14 Impact factor: 15.336

7. Ni-catalyzed reductive allylation of unactivated alkyl halides with allylic carbonates.

Authors: Yijing Dai; Fan Wu; Zhenhua Zang; Hengzhi You; Hegui Gong
Journal: Chemistry Date: 2011-12-14 Impact factor: 5.236

8. Cobalt-catalyzed direct electrochemical cross-coupling between aryl or heteroaryl halides and allylic acetates or carbonates.

Authors: Paulo Gomes; Corinne Gosmini; Jacques Périchon
Journal: J Org Chem Date: 2003-02-07 Impact factor: 4.354

9. Inter- and intramolecular palladium-catalyzed allyl cross-coupling reactions using allylindium generated in situ from allyl acetates, indium, and indium trichloride.

Authors: Dong Seomoon; Kooyeon Lee; Hyunseok Kim; Phil Ho Lee
Journal: Chemistry Date: 2007 Impact factor: 5.236

10. Functionalized arylzinc compounds in ethereal solvent: direct synthesis from aryl iodides and zinc powder and application to Pd-catalyzed reaction with allylic halides.

Authors: Ryo Ikegami; Akiko Koresawa; Takanori Shibata; Kentaro Takagi
Journal: J Org Chem Date: 2003-03-21 Impact factor: 4.354

18 in total

Selective cross-coupling of organic halides with allylic acetates.

1. Rhodium-catalyzed cross-coupling of allyl alcohols with aryl- and vinylboronic acids in ionic liquids.

2. Palladium-catalyzed alkylation-hydride reduction sequence: synthesis of meta-substituted arenes.

3. Nickel-Catalyzed Direct Electrochemical Cross-Coupling between Aryl Halides and Activated Alkyl Halides.

4. Chemistry of organomanganese(II) compounds.

5. Discovery of 4-[4-({(3R)-1-butyl-3-[(R)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undec-9-yl}methyl)phenoxy]benzoic acid hydrochloride: a highly potent orally available CCR5 selective antagonist.

6. Cobalt-catalyzed reductive allylation of alkyl halides with allylic acetates or carbonates.

7. Ni-catalyzed reductive allylation of unactivated alkyl halides with allylic carbonates.

8. Cobalt-catalyzed direct electrochemical cross-coupling between aryl or heteroaryl halides and allylic acetates or carbonates.

9. Inter- and intramolecular palladium-catalyzed allyl cross-coupling reactions using allylindium generated in situ from allyl acetates, indium, and indium trichloride.

10. Functionalized arylzinc compounds in ethereal solvent: direct synthesis from aryl iodides and zinc powder and application to Pd-catalyzed reaction with allylic halides.

1. Ni-Catalyzed Cross-Electrophile Coupling for the Synthesis of Skipped Polyenes.

2. Nickel-catalyzed reductive conjugate addition to enones via allylnickel intermediates.

3. Nickel-catalyzed cross-electrophile coupling of 2-chloropyridines with alkyl bromides.

4. Cross-Electrophile Coupling of Vinyl Halides with Alkyl Halides.

5. Reductive Decarboxylative Alkynylation of N-Hydroxyphthalimide Esters with Bromoalkynes.

6. Mizoroki-Heck Cyclizations of Amide Derivatives for the Introduction of Quaternary Centers.

7. Stereospecific Nickel-Catalyzed Reductive Cross-Coupling of Alkyl Tosylate and Allyl Alcohol Electrophiles.

8. Native functionality in triple catalytic cross-coupling: sp³ C-H bonds as latent nucleophiles.

9. Template-induced macrocycle diversity through large ring-forming alkylations of tryptophan.

10. Intramolecular carbonickelation of alkenes.