Reduction of Solid-Supported Olefins and AlkynesClick to copy article linkArticle link copied!
Abstract
The reduction of carbon−carbon multiple bonds in alkynes and olefins supported on a polystyrene resin has been investigated. Homogeneous catalysis by titanocene reagents is effective for the stereoselective preparation of cis-olefins from diarylacetylenes, while the use of copper(I) hydride reagents is effective for the reduction of α,β-unsaturated ketones.
Cited By
Smart citations by scite.ai include citation statements extracted from the full text of the citing article. The number of the statements may be higher than the number of citations provided by ACS Publications if one paper cites another multiple times or lower if scite has not yet processed some of the citing articles.
This article is cited by 16 publications.
- Adrian Wierzchowski, Donald J. Wink, Hongyang Zhang, Kristy Kambanis, Jacqueline O. Rojas Robles, Avia Rosenhouse-Dantsker. CoLab: A Workshop-Based Undergraduate Research Experience for Entering College Students. Journal of Chemical Education 2022, 99
(12)
, 4085-4093. https://doi.org/10.1021/acs.jchemed.1c01290
- Gennadii A. Grabovyi and Justin T. Mohr . Total Synthesis of Grifolin, Grifolic Acid, LL-Z1272α, LL-Z1272β, and Ilicicolinic Acid A. Organic Letters 2016, 18
(19)
, 5010-5013. https://doi.org/10.1021/acs.orglett.6b02469
- Scott A. Van Arman, Austin J. Zimmet, and Ian E. Murray . A Hantzsch Amido Dihydropyridine as a Transfer Hydrogenation Reagent for α,β-Unsaturated Ketones. The Journal of Organic Chemistry 2016, 81
(9)
, 3528-3532. https://doi.org/10.1021/acs.joc.6b00041
- Camille Oger, Laurence Balas, Thierry Durand, and Jean-Marie Galano . Are Alkyne Reductions Chemo-, Regio-, and Stereoselective Enough To Provide Pure (Z)-Olefins in Polyfunctionalized Bioactive Molecules?. Chemical Reviews 2013, 113
(3)
, 1313-1350. https://doi.org/10.1021/cr3001753
- Roland E. Dolle, Bertrand Le Bourdonnec, Karin Worm, Guillermo A. Morales, Craig J. Thomas, and Wei Zhang . Comprehensive Survey of Chemical Libraries for Drug Discovery and Chemical Biology: 2009. Journal of Combinatorial Chemistry 2010, 12
(6)
, 765-806. https://doi.org/10.1021/cc100128w
- Jay Bardole, Gabriela Weaver. Conducting Undergraduate Research at Vincennes University. Journal of Chemical Education 2010, 87
(11)
, 1131-1132. https://doi.org/10.1021/ed100696z
- Yuji Shibasaki, Tomoya Shirata, Yoshiyuki Oishi. Synthesis of Thermosetting Polycarbonate with Ethynyl Terminals. Journal of Photopolymer Science and Technology 2023, 36
(5)
, 395-401. https://doi.org/10.2494/photopolymer.36.395
- Yizhong Shi, Guanglei Li, Baodong Zhao, Yu Chen, Pengjie Chao, Huiqing Zhang, Xiaoning Wang, Tao Wang. Synthesis and optical properties of cationic cyclopentadienyl iron complexes with diphenylacetylene chromophores. Inorganica Chimica Acta 2015, 427 , 259-265. https://doi.org/10.1016/j.ica.2015.01.007
- Bart I. Roman, Jean‐Christophe Monbaliu, Laurens M. De Coen, Sigrid Verhasselt, Bart Schuddinck, Evelien Van Hoeylandt, Christian V. Stevens. Feruloylbenzotriazole and Weinreb Amide as Bioinspired Building Blocks: A Reactivity Study towards O‐, N‐, S‐, and C‐Nucleophiles. European Journal of Organic Chemistry 2014, 2014
(12)
, 2594-2611. https://doi.org/10.1002/ejoc.201301895
- DR Carbery. 8.18 Reduction of CåC and CåC by Noncatalytic Chemical Methods. 2014, 632-638. https://doi.org/10.1016/B978-0-08-097742-3.00820-X
- Manjunath Lamani, Guralamata S. Ravikumara, Kandikere Ramaiah Prabhu. Iron(III) Chloride‐Catalysed Aerobic Reduction of Olefins using Aqueous Hydrazine at Ambient Temperature. Advanced Synthesis & Catalysis 2012, 354
(8)
, 1437-1442. https://doi.org/10.1002/adsc.201200110
- Manjunath Lamani, Ravikumara Siddappa Guralamata, Kandikere Ramaiah Prabhu. Guanidine catalyzed aerobic reduction: a selective aerobic hydrogenation of olefins using aqueous hydrazine. Chemical Communications 2012, 48
(52)
, 6583. https://doi.org/10.1039/c2cc32611f
- Daniel Fürniss, Ute Schepers, Stefan Bräse. Killing double bonds softly: the reduction of polymer-bound alkenes. RSC Advances 2012, 2
(30)
, 11273. https://doi.org/10.1039/c2ra22189f
- Barrie J. Marsh, Emma L. Heath, David R. Carbery. Organocatalytic diimide reduction of enamides in water. Chem. Commun. 2011, 47
(1)
, 280-282. https://doi.org/10.1039/C0CC02272A
- Andrés A. Poeylaut-Palena, Sebastián A. Testero, Ernesto G. Mata. The non-metathetic role of Grubbs' carbene complexes: from hydrogen-free reduction of α,β-unsaturated alkenes to solid-supported sequential cross-metathesis/reduction. Chem. Commun. 2011, 47
(5)
, 1565-1567. https://doi.org/10.1039/C0CC04115G
- N.K. Terrett. Combinatorial Chemistry Online. Combinatorial Chemistry - an Online Journal 2010, 12
(3)
, 9-11. https://doi.org/10.1016/j.comche.2010.02.001
Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.
Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.
The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.