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Literature DB >> 23190029

C-C bond formation via copper-catalyzed conjugate addition reactions to enones in water at room temperature.

Bruce H Lipshutz¹, Shenlin Huang, Wendy Wen Yi Leong, Guofu Zhong, Nicholas A Isley.

Abstract

Conjugate addition reactions to enones can now be done in water at room temperature with in situ generated organocopper reagents. Mixing an enone, zinc powder, TMEDA, and an alkyl halide in a micellar environemnt containing catalytic amounts of Cu(I), Ag(I), and Au(III) leads to 1,4-adducts in good isolated yields: no organometallic precursor need be formed.

Entities: Chemical Gene Species

Mesh：

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Year: 2012 PMID： 23190029 PMCID： PMC3959802 DOI： 10.1021/ja309409e

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

26 in total

1. "On water": unique reactivity of organic compounds in aqueous suspension.

Authors: Sridhar Narayan; John Muldoon; M G Finn; Valery V Fokin; Hartmuth C Kolb; K Barry Sharpless
Journal: Angew Chem Int Ed Engl Date: 2005-05-20 Impact factor: 15.336

2. Multinuclear catalyst for copper-catalyzed asymmetric conjugate addition of organozinc reagents.

Authors: Kohei Endo; Mika Ogawa; Takanori Shibata
Journal: Angew Chem Int Ed Engl Date: 2010-03-22 Impact factor: 15.336

3. Copper-catalyzed asymmetric 1,4-addition of alkenyl alanes to N-substituted-2-3-dehydro-4-piperidones.

Authors: Daniel Müller; Alexandre Alexakis
Journal: Org Lett Date: 2012-03-15 Impact factor: 6.005

4. A practical method for enantioselective synthesis of all-carbon quaternary stereogenic centers through NHC-Cu-catalyzed conjugate additions of alkyl- and arylzinc reagents to beta-substituted cyclic enones.

Authors: Kang-sang Lee; M Kevin Brown; Alexander W Hird; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2006-06-07 Impact factor: 15.419

5. Site- and enantioselective formation of allene-bearing tertiary or quaternary carbon stereogenic centers through NHC-Cu-catalyzed allylic substitution.

Authors: Byunghyuck Jung; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2012-01-03 Impact factor: 15.419

6. Organozinc Chemistry Enabled by Micellar Catalysis. Palladium-Catalyzed Cross-Couplings between Alkyl and Aryl Bromides in Water at Room Temperature.

Authors: Christophe Duplais; Arkady Krasovskiy; Bruce H Lipshutz
Journal: Organometallics Date: 2011-11-21 Impact factor: 3.876

7. Enantioselective synthesis of allylsilanes bearing tertiary and quaternary Si-substituted carbons through Cu-catalyzed allylic alkylations with alkylzinc and arylzinc reagents.

Authors: Monica A Kacprzynski; Tricia L May; Stephanie A Kazane; Amir H Hoveyda
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

8. The first conjugate addition reaction of terminal alkynes catalytic in copper: conjugate addition of alkynes in water.

Authors: Thomas F Knöpfel; Erick M Carreira
Journal: J Am Chem Soc Date: 2003-05-21 Impact factor: 15.419

9. Zn-mediated, Pd-catalyzed cross-couplings in water at room temperature without prior formation of organozinc reagents.

Authors: Arkady Krasovskiy; Christophe Duplais; Bruce H Lipshutz
Journal: J Am Chem Soc Date: 2009-11-04 Impact factor: 15.419

C-C bond formation via copper-catalyzed conjugate addition reactions to enones in water at room temperature.

1. "On water": unique reactivity of organic compounds in aqueous suspension.

2. Multinuclear catalyst for copper-catalyzed asymmetric conjugate addition of organozinc reagents.

3. Copper-catalyzed asymmetric 1,4-addition of alkenyl alanes to N-substituted-2-3-dehydro-4-piperidones.

4. A practical method for enantioselective synthesis of all-carbon quaternary stereogenic centers through NHC-Cu-catalyzed conjugate additions of alkyl- and arylzinc reagents to beta-substituted cyclic enones.

5. Site- and enantioselective formation of allene-bearing tertiary or quaternary carbon stereogenic centers through NHC-Cu-catalyzed allylic substitution.

6. Organozinc Chemistry Enabled by Micellar Catalysis. Palladium-Catalyzed Cross-Couplings between Alkyl and Aryl Bromides in Water at Room Temperature.

7. Enantioselective synthesis of allylsilanes bearing tertiary and quaternary Si-substituted carbons through Cu-catalyzed allylic alkylations with alkylzinc and arylzinc reagents.

8. The first conjugate addition reaction of terminal alkynes catalytic in copper: conjugate addition of alkynes in water.

9. Zn-mediated, Pd-catalyzed cross-couplings in water at room temperature without prior formation of organozinc reagents.

10. The role of silver additives in gold-mediated C-H functionalisation.

1. A chemical biology route to site-specific authentic protein modifications.

2. Dehalogenation of Functionalized Alkyl Halides in Water at Room Temperature.

Review 3. En route to metal-mediated and metal-catalysed reactions in water.

4. Leveraging the micellar effect: gold-catalyzed dehydrative cyclizations in water at room temperature.

5. Transitioning organic synthesis from organic solvents to water. What's your E Factor?

6. A modular phosphate tether-mediated divergent strategy to complex polyols.