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Literature DB >> 19206518

Au(I)-Catalyzed cycloisomerizations terminated by sp(3) C-H bond insertion.

Yoshikazu Horino¹, Takuya Yamamoto, Kohki Ueda, Shigeyasu Kuroda, F Dean Toste.

Abstract

The gold(I)-catalyzed cycloisomerization of 1,5-enynes and 1,4-allylallenes to tetracyclododecane and tetracyclotridecane derivatives, respectively, is reported. Complexation of the cationic gold(I) complex to either the alkyne or allene moiety induces an intramolecular addition of the alkene, leading to a gold(I)-stabilized carbenoid intermediate. This intermediate undergoes a formal sp(3) C-H insertion to generate the tetracyclic adduct. A series of deuterium labeling experiments showed that the C-H functionalization step proceeds with an inverse kinetic isotope effect.

Entities: Chemical Gene

Mesh：

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Year: 2009 PMID： 19206518 PMCID： PMC2880645 DOI： 10.1021/ja808780r

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

32 in total

1. Primary semiclassical kinetic hydrogen isotope effects in identity carbon-to-carbon proton- and hydride-transfer reactions, an ab initio and DFT computational study.

Authors: Scott Gronert; James R Keeffe
Journal: J Org Chem Date: 2006-08-04 Impact factor: 4.354

2. Room-temperature Au(I)-catalyzed C-C bond formation through a tandem Friedel-Crafts-type addition/carbocyclization reaction.

Authors: Patrick Yves Toullec; Emilie Genin; Lucie Leseurre; Jean-Pierre Genêt; Véronique Michelet
Journal: Angew Chem Int Ed Engl Date: 2006-11-13 Impact factor: 15.336

3. Rearrangement of alkynyl sulfoxides catalyzed by gold(I) complexes.

Authors: Nathan D Shapiro; F Dean Toste
Journal: J Am Chem Soc Date: 2007-03-20 Impact factor: 15.419

4. Gold(I)-catalyzed [2 + 2]-cycloaddition of allenenes.

Authors: Michael R Luzung; Pablo Mauleón; F Dean Toste
Journal: J Am Chem Soc Date: 2007-09-21 Impact factor: 15.419

5. Gold-catalyzed 1,3-addition of a sp3-hybridized C-H bond to alkenylcarbenoid intermediate.

Authors: Sabyasachi Bhunia; Rai-Shung Liu
Journal: J Am Chem Soc Date: 2008-12-10 Impact factor: 15.419

6. On the nature of the reactive intermediates in gold-catalyzed cycloisomerization reactions.

Authors: Alois Fürstner; Louis Morency
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

7. Activation of methane by gold cations: guided ion beam and theoretical studies.

Authors: Feng-Xia Li; P B Armentrout
Journal: J Chem Phys Date: 2006-10-07 Impact factor: 3.488

8. Reactions of carbocations with unsaturated hydrocarbons: electrophilic alkylation or hydride abstraction?

Authors: Herbert Mayr; Gabriele Lang; Armin R Ofial
Journal: J Am Chem Soc Date: 2002-04-17 Impact factor: 15.419

9. Cycloisomerization of 1,n-enynes: challenging metal-catalyzed rearrangements and mechanistic insights.

Authors: Véronique Michelet; Patrick Y Toullec; Jean-Pierre Genêt
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

10. Alkyne versus allene activation in platinum- and gold-catalyzed cycloisomerization of hydroxylated 1,5-allenynes.

Authors: Riadh Zriba; Vincent Gandon; Corinne Aubert; Louis Fensterbank; Max Malacria
Journal: Chemistry Date: 2008 Impact factor: 5.236

14 in total

1. Computationally guided stereocontrol of the combined C-H functionalization/Cope rearrangement.

Authors: Yajing Lian; Kenneth I Hardcastle; Huw M L Davies
Journal: Angew Chem Int Ed Engl Date: 2011-08-30 Impact factor: 15.336

2. A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions.

Authors: Nathan D Shapiro; F Dean Toste
Journal: Synlett Date: 2010-03-01 Impact factor: 2.454

3. Experimental and computational evidence for gold vinylidenes: generation from terminal alkynes via a bifurcation pathway and facile C-H insertions.

Authors: Longwu Ye; Yanzhao Wang; Donald H Aue; Liming Zhang
Journal: J Am Chem Soc Date: 2011-12-28 Impact factor: 15.419

Au(I)-Catalyzed cycloisomerizations terminated by sp(3) C-H bond insertion.

1. Primary semiclassical kinetic hydrogen isotope effects in identity carbon-to-carbon proton- and hydride-transfer reactions, an ab initio and DFT computational study.

2. Room-temperature Au(I)-catalyzed C-C bond formation through a tandem Friedel-Crafts-type addition/carbocyclization reaction.

3. Rearrangement of alkynyl sulfoxides catalyzed by gold(I) complexes.

4. Gold(I)-catalyzed [2 + 2]-cycloaddition of allenenes.

5. Gold-catalyzed 1,3-addition of a sp3-hybridized C-H bond to alkenylcarbenoid intermediate.

6. On the nature of the reactive intermediates in gold-catalyzed cycloisomerization reactions.

7. Activation of methane by gold cations: guided ion beam and theoretical studies.

8. Reactions of carbocations with unsaturated hydrocarbons: electrophilic alkylation or hydride abstraction?

9. Cycloisomerization of 1,n-enynes: challenging metal-catalyzed rearrangements and mechanistic insights.

10. Alkyne versus allene activation in platinum- and gold-catalyzed cycloisomerization of hydroxylated 1,5-allenynes.

1. Computationally guided stereocontrol of the combined C-H functionalization/Cope rearrangement.

2. A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions.

3. Experimental and computational evidence for gold vinylidenes: generation from terminal alkynes via a bifurcation pathway and facile C-H insertions.

4. C-C Bond Migration in the Cycloisomerization of 1,6-Enynes.

5. BF₃-Promoted, Carbene-like, C-H Insertion Reactions of Benzynes.

6. Asymmetric Au-catalyzed cycloisomerization of 1,6-enynes: An entry to bicyclo[4.1.0]heptene.

7. Recent advances in the gold-catalyzed additions to C-C multiple bonds.

8. Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity.

9. A bonding model for gold(I) carbene complexes.

10. Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinyl carboxylic acids via a radical process.