Literature DB >> 29062586

"Cut and Sew" Transformations via Transition-Metal-Catalyzed Carbon-Carbon Bond Activation.

Peng-Hao Chen1, Brent A Billett2, Tatsuhiro Tsukamoto2, Guangbin Dong2.   

Abstract

The transition class="Chemical">metal-catalyzed "cut and sew" transformation has recently emerged as a useful strategy for preparing <class="Chemical">span class="Chemical">complex molecular structures. After oxidative addition of a transition metal into a carbon-carbon bond, the resulting two carbon termini can be both functionalized in one step via the following migratory insertion and reductive elimination with unsaturated units, such as alkenes, alkynes, allenes, CO and polar multiple bonds. Three- or four-membered rings are often employed as reaction partners due to their high ring strains. The participation of non-strained structures generally relies on cleavage of a polar carbon-CN bond or assistance of a directing group.

Entities:  

Keywords:  carbon–carbon activation; cut and sew; oxidative addition; reductive elimination; transition-metal catalysis

Year:  2017        PMID: 29062586      PMCID: PMC5650109          DOI: 10.1021/acscatal.6b03210

Source DB:  PubMed          Journal:  ACS Catal            Impact factor:   13.084


  101 in total

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2.  Synthesis of aromatic compounds by catalytic C-C bond activation of biphenylene or angular [3]phenylene.

Authors:  Aleš Korotvička; Ivana Císařová; Jana Roithová; Martin Kotora
Journal:  Chemistry       Date:  2012-03-12       Impact factor: 5.236

3.  Transition metal chemistry of cyclopropenes and cyclopropanes.

Authors:  Michael Rubin; Marina Rubina; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2007-07       Impact factor: 60.622

4.  Progress in the synthesis and transformations of alkylidenecyclopropanes and alkylidenecyclobutanes.

Authors:  Alberto Brandi; Stefano Cicchi; Franca M Cordero; Andrea Goti
Journal:  Chem Rev       Date:  2014-06-13       Impact factor: 60.622

5.  Highly enantioselective rhodium(I)-catalyzed carbonyl carboacylations initiated by C-C bond activation.

Authors:  Laetitia Souillart; Nicolai Cramer
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-14       Impact factor: 15.336

6.  Palladium-catalyzed C-CN activation for intramolecular cyanoesterification of alkynes.

Authors:  Naveen R Rondla; Samuel M Levi; Jonathan M Ryss; Rachel A Vanden Berg; Christopher J Douglas
Journal:  Org Lett       Date:  2011-03-21       Impact factor: 6.005

7.  Cyclobutanes in catalysis.

Authors:  Tobias Seiser; Tanguy Saget; Duc N Tran; Nicolai Cramer
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-26       Impact factor: 15.336

8.  Formal synthesis of (±)-galanthamine and (±)-lycoramine using Rh(I)-catalyzed [(3 + 2) + 1] cycloaddition of 1-ene-vinylcyclopropane and CO.

Authors:  Yu Feng; Zhi-Xiang Yu
Journal:  J Org Chem       Date:  2015-01-16       Impact factor: 4.354

9.  Cyclopentadienone synthesis by rhodium(I)-catalyzed [3 + 2] cycloaddition reactions of cyclopropenones and alkynes.

Authors:  Paul A Wender; Thomas J Paxton; Travis J Williams
Journal:  J Am Chem Soc       Date:  2006-11-22       Impact factor: 15.419

10.  A computationally designed Rh(I)-catalyzed two-component [5+2+1] cycloaddition of ene-vinylcyclopropanes and CO for the synthesis of cyclooctenones.

Authors:  Yuanyuan Wang; Jingxin Wang; Jiachun Su; Feng Huang; Lei Jiao; Yong Liang; Dazhi Yang; Shiwei Zhang; Paul A Wender; Zhi-Xiang Yu
Journal:  J Am Chem Soc       Date:  2007-07-27       Impact factor: 15.419

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  48 in total

Review 1.  Transition Metal-Mediated C-C Single Bond Cleavage: Making the Cut in Total Synthesis.

Authors:  Brian Wang; Melecio A Perea; Richmond Sarpong
Journal:  Angew Chem Int Ed Engl       Date:  2020-08-24       Impact factor: 15.336

2.  Suzuki-Miyaura Coupling of Simple Ketones via Activation of Unstrained Carbon-Carbon Bonds.

Authors:  Ying Xia; Jianchun Wang; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2018-04-17       Impact factor: 15.419

3.  Intramolecular Acetyl Transfer to Olefins by Catalytic C-C Bond Activation of Unstrained Ketones.

Authors:  Zi-Qiang Rong; Hee Nam Lim; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2017-12-08       Impact factor: 15.336

4.  Kinetic Resolution via Rh-Catalyzed C-C Activation of Cyclobutanones at Room Temperature.

Authors:  Lin Deng; Yue Fu; Siu Yin Lee; Chengpeng Wang; Peng Liu; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2019-10-02       Impact factor: 15.419

5.  Catalytic Ring Expansions of Cyclic Alcohols Enabled by Proton-Coupled Electron Transfer.

Authors:  Kuo Zhao; Kenji Yamashita; Joseph E Carpenter; Trevor C Sherwood; William R Ewing; Peter T W Cheng; Robert R Knowles
Journal:  J Am Chem Soc       Date:  2019-05-23       Impact factor: 15.419

6.  Palladium-catalysed carboformylation of alkynes using acid chlorides as a dual carbon monoxide and carbon source.

Authors:  Yong Ho Lee; Elliott H Denton; Bill Morandi
Journal:  Nat Chem       Date:  2021-01-29       Impact factor: 24.427

7.  Activation of diverse carbon-heteroatom and carbon-carbon bonds via palladium(II)-catalysed β-X elimination.

Authors:  Van T Tran; John A Gurak; Kin S Yang; Keary M Engle
Journal:  Nat Chem       Date:  2018-08-20       Impact factor: 24.427

8.  Cobalt-Catalyzed Reductive Dimethylcyclopropanation of 1,3-Dienes.

Authors:  Jacob Werth; Christopher Uyeda
Journal:  Angew Chem Int Ed Engl       Date:  2018-09-25       Impact factor: 15.336

Review 9.  Ruthenium(0)-Catalyzed Cycloaddition of 1,2-Diols, Ketols, or Diones via Alcohol-Mediated Hydrogen Transfer.

Authors:  Hiroki Sato; Ben W H Turnbull; Keisuke Fukaya; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2018-02-06       Impact factor: 15.336

10.  Fused-Ring Formation by an Intramolecular "Cut-and-Sew" Reaction between Cyclobutanones and Alkynes.

Authors:  Lin Deng; Likun Jin; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2018-02-06       Impact factor: 15.336

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