Literature DB >> 25608143

Alkyne hydroacylation: switching regioselectivity by tandem ruthenium catalysis.

Qing-An Chen1, Faben A Cruz, Vy M Dong.   

Abstract

By using tandem Ru-catalysis, internal alkynes can be coupled with aldehydes for the synthesis of β,γ-unsaturated ketones. The catalyst promotes alkyne transformations with high regioselectivity, with examples that include the differentiation of a methyl vs ethyl substituent on the alkyne. Mechanistic studies suggest that the regioselectivity results from a selective allene formation that is governed by allylic strain.

Entities:  

Mesh：

Substances：

Year:  2015        PMID： 25608143      PMCID： PMC4445957          DOI： 10.1021/ja512015w

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


  54 in total

1.  A versatile new method for the synthesis of cyclopentenones via an unusual rhodium-catalyzed intramolecular trans hydroacylation of an alkyne.

Authors:  K Tanaka; G C Fu
Journal:  J Am Chem Soc       Date:  2001-11-21       Impact factor: 15.419

Review 2.  Ruthenium-based heterocyclic carbene-coordinated olefin metathesis catalysts.

Authors:  Georgios C Vougioukalakis; Robert H Grubbs
Journal:  Chem Rev       Date:  2010-03-10       Impact factor: 60.622

3.  Grubbs' ruthenium-carbenes beyond the metathesis reaction: less conventional non-metathetic utility.

Authors:  Benito Alcaide; Pedro Almendros; Amparo Luna
Journal:  Chem Rev       Date:  2009-08       Impact factor: 60.622

4.  Redox-neutral atom-economic rhodium-catalyzed coupling of terminal alkynes with carboxylic acids toward branched allylic esters.

Authors:  Alexandre Lumbroso; Philipp Koschker; Nicolas R Vautravers; Bernhard Breit
Journal:  J Am Chem Soc       Date:  2011-02-03       Impact factor: 15.419

5.  An alkyne hydroacylation route to highly substituted furans.

Authors:  Philip Lenden; David A Entwistle; Michael C Willis
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-20       Impact factor: 15.336

6.  Gold(I)-catalyzed diastereoselective hydroacylation of terminal alkynes with glyoxals.

Authors:  Shuai Shi; Tao Wang; Vanessa Weingand; Matthias Rudolph; A Stephen K Hashmi
Journal:  Angew Chem Int Ed Engl       Date:  2013-12-11       Impact factor: 15.336

7.  Rhodium-catalysed linear-selective alkyne hydroacylation.

Authors:  Sarah-Jane Poingdestre; Jonathan D Goodacre; Andrew S Weller; Michael C Willis
Journal:  Chem Commun (Camb)       Date:  2012-05-22       Impact factor: 6.222

8.  Parallel kinetic resolution of 4-alkynals catalyzed by Rh(I)/Tol-BINAP: synthesis of enantioenriched cyclobutanones and cyclopentenones.

Authors:  Ken Tanaka; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2003-07-09       Impact factor: 15.419

9.  Successive C-C coupling of dienes to vicinally dioxygenated hydrocarbons: ruthenium catalyzed [4 + 2] cycloaddition across the diol, hydroxycarbonyl, or dione oxidation levels.

Authors:  Laina M Geary; Ben W Glasspoole; Mary M Kim; Michael J Krische
Journal:  J Am Chem Soc       Date:  2013-02-28       Impact factor: 15.419

10.  Ruthenium hydride-catalyzed addition of aldehydes to dienes leading to beta,gamma-unsaturated ketones.

Authors:  Sohei Omura; Takahide Fukuyama; Jiro Horiguchi; Yuji Murakami; Ilhyong Ryu
Journal:  J Am Chem Soc       Date:  2008-10-08       Impact factor: 15.419
View more
  17 in total

1.  Mechanisms for nickel(0)/N-heterocyclic carbene-catalyzed intramolecular alkene hydroacylation: insights from a DFT study.

Authors:  Qingxi Meng; Fen Wang
Journal:  J Mol Model       Date:  2016-12-21       Impact factor: 1.810

2.  Rhodium-Catalyzed Enantioselective Hydroamination of Alkynes with Indolines.

Authors:  Qing-An Chen; Zhiwei Chen; Vy M Dong
Journal:  J Am Chem Soc       Date:  2015-06-29       Impact factor: 15.419

3.  Tandem rhodium catalysis: exploiting sulfoxides for asymmetric transition-metal catalysis.

Authors:  K G M Kou; V M Dong
Journal:  Org Biomol Chem       Date:  2015-06-07       Impact factor: 3.876

4.  Enantioselective ruthenium-catalyzed carbonyl allylation via alkyne-alcohol C-C bond-forming transfer hydrogenation: allene hydrometalation vs oxidative coupling.

Authors:  Tao Liang; Khoa D Nguyen; Wandi Zhang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-03-03       Impact factor: 15.419

5.  Alkyne Hydroheteroarylation: Enantioselective Coupling of Indoles and Alkynes via Rh-Hydride Catalysis.

Authors:  Faben A Cruz; Yamin Zhu; Quentin D Tercenio; Zengming Shen; Vy M Dong
Journal:  J Am Chem Soc       Date:  2017-07-25       Impact factor: 15.419

6.  Mechanisms and reactivity differences for the cobalt-catalyzed enantioselective intramolecular hydroacylation of ketones and alkenes: insights from density functional calculations.

Authors:  Qingxi Meng; Fen Wang
Journal:  J Mol Model       Date:  2016-02-18       Impact factor: 1.810

7.  Tandem Rh-catalysis: decarboxylative β-keto acid and alkyne cross-coupling.

Authors:  Faben A Cruz; Zhiwei Chen; Sarah I Kurtoic; Vy M Dong
Journal:  Chem Commun (Camb)       Date:  2016-04-04       Impact factor: 6.222

8.  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

9.  Stereodivergent Coupling of Aldehydes and Alkynes via Synergistic Catalysis Using Rh and Jacobsen's Amine.

Authors:  Faben A Cruz; Vy M Dong
Journal:  J Am Chem Soc       Date:  2017-01-11       Impact factor: 16.383

10.  Sequential Catalytic Functionalization of Aryltriazenyl Aldehydes for the Synthesis of Complex Benzenes.

Authors:  Sangwon Seo; Ming Gao; Eva Paffenholz; Michael C Willis
Journal:  ACS Catal       Date:  2021-05-05       Impact factor: 13.084
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.