Literature DB >> 28605083

Alkynes as Electrophilic or Nucleophilic Allylmetal Precursors in Transition-Metal Catalysis.

Alexander M Haydl1, Bernhard Breit1, Tao Liang2, Michael J Krische2.   

Abstract

Diverse late transition class="Chemical">metal catalysts convert terminal or internal <class="Chemical">span class="Chemical">alkynes into transient allylmetal species that display electrophilic or nucleophilic properties. Whereas classical methods for the generation of allylmetal species often form stoichiometric by-products, the recent use of alkynes as allylmetal precursors enables completely atom-efficient catalytic processes to be carried out, including enantioselective transformations.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkynes; allylation; catalysis; electrophiles; nucleophiles

Mesh：

Substances：

Year:  2017        PMID： 28605083      PMCID： PMC5637541          DOI： 10.1002/anie.201704248

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  106 in total

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Authors:  Frauke Pohlki; Sven Doye
Journal:  Chem Soc Rev       Date:  2003-03       Impact factor: 54.564

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Authors:  Thomas E Müller; Kai C Hultzsch; Miguel Yus; Francisco Foubelo; Mizuki Tada
Journal:  Chem Rev       Date:  2008-08-26       Impact factor: 60.622

3.  A highly enantioselective allylic amination reaction using a commercially available chiral rhodium catalyst: resolution of racemic allylic carbonates.

Authors:  Derek C Vrieze; Garrett S Hoge; Perrine Z Hoerter; Jared T Van Haitsma; Brian M Samas
Journal:  Org Lett       Date:  2009-07-16       Impact factor: 6.005

4.  A palladium-catalyzed three-component cross-coupling of conjugated dienes or terminal alkenes with vinyl triflates and boronic acids.

Authors:  Longyan Liao; Ranjan Jana; Kaveri Balan Urkalan; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2011-03-30       Impact factor: 15.419

5.  Unlocking Hydrogenation for C-C Bond Formation: A Brief Overview of Enantioselective Methods.

Authors:  Abbas Hassan; Michael J Krische
Journal:  Org Process Res Dev       Date:  2011-11-18       Impact factor: 3.317

6.  One pot iridium-catalyzed asymmetrical double allylations of sodium sulfide: a fast and economic way to construct chiral C2-symmetric bis(1-substituted-allyl)sulfane.

Authors:  Shengcai Zheng; Weiqing Huang; Ning Gao; Ruimin Cui; Min Zhang; Xiaoming Zhao
Journal:  Chem Commun (Camb)       Date:  2011-05-18       Impact factor: 6.222

7.  Palladium-Catalyzed Dearomative Allylic Alkylation of Indoles with Alkynes To Synthesize Indolenines with C3-Quarternary Centers.

Authors:  Shang Gao; Zijun Wu; Xinxin Fang; Aijun Lin; Hequan Yao
Journal:  Org Lett       Date:  2016-07-21       Impact factor: 6.005

8.  Regioconvergent and Enantioselective Rhodium-Catalyzed Hydroamination of Internal and Terminal Alkynes: A Highly Flexible Access to Chiral Pyrazoles.

Authors:  Alexander M Haydl; Lukas J Hilpert; Bernhard Breit
Journal:  Chemistry       Date:  2016-04-01       Impact factor: 5.236

9.  Direct, redox-neutral prenylation and geranylation of secondary carbinol C-H bonds: C4-regioselectivity in ruthenium-catalyzed C-C couplings of dienes to α-hydroxy esters.

Authors:  Joyce C Leung; Laina M Geary; Te-Yu Chen; Jason R Zbieg; Michael J Krische
Journal:  J Am Chem Soc       Date:  2012-09-17       Impact factor: 15.419

10.  Rhodium-catalyzed chemo- and regioselective decarboxylative addition of β-ketoacids to alkynes.

Authors:  Changkun Li; Christian P Grugel; Bernhard Breit
Journal:  Chem Commun (Camb)       Date:  2016-04-04       Impact factor: 6.222
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  18 in total

1.  Catalytic Hydrothiolation: Regio- and Enantioselective Coupling of Thiols and Dienes.

Authors:  Xiao-Hui Yang; Ryan T Davison; Vy M Dong
Journal:  J Am Chem Soc       Date:  2018-08-09       Impact factor: 15.419

2.  Catalytic Hydrothiolation: Counterion-Controlled Regioselectivity.

Authors:  Xiao-Hui Yang; Ryan T Davison; Shao-Zhen Nie; Faben A Cruz; Tristan M McGinnis; Vy M Dong
Journal:  J Am Chem Soc       Date:  2019-02-08       Impact factor: 15.419

3.  Carbonyl anti-(α-Amino)allylation via Ruthenium Catalyzed Hydrogen Autotransfer: Use of an Acetylenic Pyrrole as an Allylmetal Pronucleophile.

Authors:  Wandi Zhang; Weijie Chen; Hongde Xiao; Michael J Krische
Journal:  Org Lett       Date:  2017-08-29       Impact factor: 6.005

Review 4.  Intermolecular Metal-Catalyzed Reductive Coupling of Dienes, Allenes, and Enynes with Carbonyl Compounds and Imines.

Authors:  Michael Holmes; Leyah A Schwartz; Michael J Krische
Journal:  Chem Rev       Date:  2018-06-13       Impact factor: 60.622

5.  Diastereo- and Enantioselective Ruthenium-Catalyzed C-C Coupling of 1-Arylpropynes and Alcohols: Alkynes as Chiral Allylmetal Precursors in Carbonyl anti-(α-Aryl)allylation.

Authors:  Ming Xiang; Ankan Ghosh; Michael J Krische
Journal:  J Am Chem Soc       Date:  2021-02-08       Impact factor: 15.419

6.  Enantioselective Addition of α-Nitroesters to Alkynes.

Authors:  Ryan T Davison; Patrick D Parker; Xintong Hou; Crystal P Chung; Sara A Augustine; Vy M Dong
Journal:  Angew Chem Int Ed Engl       Date:  2021-01-07       Impact factor: 15.336

7.  Reducing Challenges in Organic Synthesis with Stereoselective Hydrogenation and Tandem Catalysis.

Authors:  Patrick D Parker; Xintong Hou; Vy M Dong
Journal:  J Am Chem Soc       Date:  2021-04-23       Impact factor: 16.383

8.  Understanding Halide Counterion Effects in Enantioselective Ruthenium-Catalyzed Carbonyl (α-Aryl)allylation: Alkynes as Latent Allenes and Trifluoroethanol-Enhanced Turnover in The Conversion of Ethanol to Higher Alcohols via Hydrogen Auto-transfer.

Authors:  Eliezer Ortiz; Jonathan Z Shezaf; Yu-Hsiang Chang; Théo P Gonçalves; Kuo-Wei Huang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2021-10-04       Impact factor: 16.383

9.  From Hydrogenation to Transfer Hydrogenation to Hydrogen Auto-Transfer in Enantioselective Metal-Catalyzed Carbonyl Reductive Coupling: Past, Present, and Future.

Authors:  Catherine Gazolla Santana; Michael J Krische
Journal:  ACS Catal       Date:  2021-04-22       Impact factor: 13.084

Review 10.  Allenes and Dienes as Chiral Allylmetal Pronucleophiles in Catalytic Enantioselective C=X Addition: Historical Perspective and State-of-The-Art Survey.

Authors:  Ming Xiang; Dana E Pfaffinger; Michael J Krische
Journal:  Chemistry       Date:  2021-07-29       Impact factor: 5.020
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