Literature DB >> 26295504

Phosphine-Mediated Iterative Arene Homologation Using Allenes.

Kui Zhang1, Lingchao Cai1, Xing Jiang1, Miguel A Garcia-Garibay1, Ohyun Kwon1.   

Abstract

A PPh3-mediated multicomponent reaction between o-phthalaldehydes, nucleophiles, and monosubstituted allenes furnishes functionalized non-C2-symmetric naphthalenes in synthetically useful yields. When the o-phthalaldehydes were reacted with 1,3-disubstituted allenes in the presence of PPh2Et, naphthalene derivatives were also obtained in up to quantitative yields. The mechanism of the latter transformation is straightforward: aldol addition followed by Wittig olefination and dehydration. The mechanism of the former is a tandem γ-umpolung/aldol/Wittig/dehydration process, as established by preparation of putative reaction intermediates and mass spectrometric analysis. This transformation can be applied iteratively to prepare anthracenes and tetracenes using carboxylic acids as pronucleophiles.

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Year:  2015        PMID： 26295504      PMCID： PMC4915745          DOI： 10.1021/jacs.5b07403

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


  43 in total

1.  Versatile enantioselective [3+2] cyclization between imines and allenoates catalyzed by dipeptide-based phosphines.

Authors:  Xiaoyu Han; Fangrui Zhong; Youqing Wang; Yixin Lu
Journal:  Angew Chem Int Ed Engl       Date:  2011-12-07       Impact factor: 15.336

2.  Bifunctional phosphine-catalyzed domino reaction: highly stereoselective synthesis of cis-2,3-dihydrobenzofurans from salicyl N-thiophosphinyl imines and allenes.

Authors:  Xiangtai Meng; You Huang; Ruyu Chen
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005

3.  An unexpected phosphine-catalyzed [3 + 2] annulation. Synthesis of highly functionalized cyclopentenes.

Authors:  Zheng Lu; Suqing Zheng; Xumu Zhang; Xiyan Lu
Journal:  Org Lett       Date:  2008-07-03       Impact factor: 6.005

4.  Theoretical rationale for regioselection in phosphine-catalyzed allenoate additions to acrylates, imines, and aldehydes.

Authors:  Travis Dudding; Ohyun Kwon; Evan Mercier
Journal:  Org Lett       Date:  2006-08-17       Impact factor: 6.005

5.  Asymmetric [3+2] cycloadditions of allenoates and dual activated olefins catalyzed by simple bifunctional N-acyl aminophosphines.

Authors:  Hua Xiao; Zhuo Chai; Chang-Wu Zheng; Ying-Quan Yang; Wen Liu; Jun-Kang Zhang; Gang Zhao
Journal:  Angew Chem Int Ed Engl       Date:  2010-06-14       Impact factor: 15.336

6.  Synthesis of naphthalenes via platinum-catalyzed hydroarylation of aryl enynes.

Authors:  Dongjin Kang; Jinsik Kim; Susung Oh; Phil Ho Lee
Journal:  Org Lett       Date:  2012-10-25       Impact factor: 6.005

7.  Beyond the aza-Morita-Baylis-Hillman reaction: Lewis base-catalyzed reactions of N-Boc-imines with ethyl 2,3-butadienoate.

Authors:  Xiao-Yang Guan; Yin Wei; Min Shi
Journal:  J Org Chem       Date:  2009-08-21       Impact factor: 4.354

8.  Catalytic asymmetric C-N bond formation: phosphine-catalyzed intra- and intermolecular γ-addition of nitrogen nucleophiles to allenoates and alkynoates.

Authors:  Rylan J Lundgren; Ashraf Wilsily; Nicolas Marion; Cong Ma; Ying Kit Chung; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-21       Impact factor: 15.336

9.  The dynamics of singlet fission in crystalline tetracene and covalent analogs.

Authors:  Jonathan J Burdett; Christopher J Bardeen
Journal:  Acc Chem Res       Date:  2013-01-29       Impact factor: 22.384

10.  Phosphine-mediated olefination between aldehydes and allenes: an efficient synthesis of trisubstituted 1,3-dienes with high E-selectivity.

Authors:  Silong Xu; Lili Zhou; San Zeng; Renqin Ma; Zhihong Wang; Zhengjie He
Journal:  Org Lett       Date:  2009-08-06       Impact factor: 6.005
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  6 in total

Review 1.  The Molecular Industrial Revolution: Automated Synthesis of Small Molecules.

Authors:  Melanie Trobe; Martin D Burke
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-07       Impact factor: 15.336

2.  Toward Generalization of Iterative Small Molecule Synthesis.

Authors:  Jonathan W Lehmann; Daniel J Blair; Martin D Burke
Journal:  Nat Rev Chem       Date:  2018-03-07       Impact factor: 34.035

3.  From Mechanistic Study to Chiral Catalyst Optimization: Theoretical Insight into Binaphthophosphepine-catalyzed Asymmetric Intramolecular [3 + 2] Cycloaddition.

Authors:  Meng Duan; Lei Zhu; Xiaotian Qi; Zhaoyuan Yu; Yingzi Li; Ruopeng Bai; Yu Lan
Journal:  Sci Rep       Date:  2017-08-08       Impact factor: 4.379

4.  Bridged [2.2.1] bicyclic phosphine oxide facilitates catalytic γ-umpolung addition-Wittig olefination.

Authors:  Kui Zhang; Lingchao Cai; Zhongyue Yang; K N Houk; Ohyun Kwon
Journal:  Chem Sci       Date:  2018-01-18       Impact factor: 9.825

5.  Helicene synthesis by Brønsted acid-catalyzed cycloaromatization in HFIP [(CF3)2CHOH].

Authors:  Takeshi Fujita; Noriaki Shoji; Nao Yoshikawa; Junji Ichikawa
Journal:  Beilstein J Org Chem       Date:  2021-02-09       Impact factor: 2.883

6.  Iterative Assembly of Macrocyclic Lactones using Successive Ring Expansion Reactions.

Authors:  Thomas C Stephens; Aggie Lawer; Thomas French; William P Unsworth
Journal:  Chemistry       Date:  2018-08-19       Impact factor: 5.236
  6 in total

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