Literature DB >> 30084247

Tandem Catalysis: Transforming Alcohols to Alkenes by Oxidative Dehydroxymethylation.

Xuesong Wu1,2, Faben A Cruz1, Alexander Lu1, Vy M Dong1.   

Abstract

We report a Rh-catalyst for accessing olefins from primary alcohols by a C-C bond cleavage that results in dehomologation. This functional group interconversion proceeds by an oxidation-dehydroformylation enabled by N, N-dimethylacrylamide as a sacrificial acceptor of hydrogen gas. Alcohols with diverse functionality and structure undergo oxidative dehydroxymethylation to access the corresponding olefins. Our catalyst protocol enables a two-step semisynthesis of (+)-yohimbenone and dehomologation of feedstock olefins.

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Year:  2018        PMID: 30084247      PMCID: PMC6619493          DOI: 10.1021/jacs.8b06069

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


  8 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.  Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones.

Authors:  Xukai Zhou; Yan Xu; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2021-11-22       Impact factor: 16.383

Review 3.  Teaching Aldehydes New Tricks Using Rhodium- and Cobalt-Hydride Catalysis.

Authors:  Ryan T Davison; Erin L Kuker; Vy M Dong
Journal:  Acc Chem Res       Date:  2021-02-03       Impact factor: 22.384

4.  Conversion of Medium-Sized Lactams to α-Vinyl or α-Acetylenyl Azacycles via N,O-Acetal TMS Ethers.

Authors:  Minjun Kim; Jaebong Jang; Goyoung Choi; Sungkyun Chung; Changjin Lim; Joonseong Hur; Hyun Su Kim; Younghwa Na; Woo Sung Son; Young-Ger Suh; Jong-Wha Jung; Seok-Ho Kim
Journal:  Molecules       Date:  2018-11-19       Impact factor: 4.411

5.  Ligand-Promoted Iridium-Catalyzed Transfer Hydrogenation of Terminal Alkynes with Ethanol and Its Application.

Authors:  Chengniu Wang; Shengnan Gong; Zhipeng Liang; Yufeng Sun; Rui Cheng; Banghua Yang; Yirong Liu; Jinfei Yang; Fei Sun
Journal:  ACS Omega       Date:  2019-09-18

6.  Visible-light-induced transition metal and photosensitizer free decarbonylative addition of amino-arylaldehydes to ketones.

Authors:  Yi Wang; Yatao Lang; Chao-Jun Li; Huiying Zeng
Journal:  Chem Sci       Date:  2021-12-21       Impact factor: 9.825

7.  Bioinspired desaturation of alcohols enabled by photoredox proton-coupled electron transfer and cobalt dual catalysis.

Authors:  Long Huang; Tengfei Ji; Chen Zhu; Huifeng Yue; Nursaya Zhumabay; Magnus Rueping
Journal:  Nat Commun       Date:  2022-02-10       Impact factor: 17.694

8.  Chemoselective Alpha-Deuteration of Amides via Retro-ene Reaction.

Authors:  Vincent Porte; Giovanni Di Mauro; Manuel Schupp; Daniel Kaiser; Nuno Maulide
Journal:  Chemistry       Date:  2020-11-17       Impact factor: 5.020

  8 in total

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