Literature DB >> 33883783

A decade review of triphosgene and its applications in organic reactions.

Moshood O Ganiu1, Binod Nepal1, Joshua P Van Houten1, Rendy Kartika1.   

Abstract

This review article highlights selected advances in triphosgene-enabled organic synthetic reactions that were reported in the decade of 2010-2019. Triphosgene is a versatile reagent in organic synthesis. It serves as a convenient substitute for the toxic phosgene gas. Despite its first known preparation in the late 19th interestingly began only three decades ago. Despite the relatively short history, triphosgene has been proven to be very useful in facilitating the preparation of a vast scope of value-added compounds, such as organohalides, acid chlorides, isocyanates, carbonyl addition adducts, heterocycles, among others. Furthermore, applications of triphosgene in complex molecules synthesis, polymer synthesis, and other techniques, such as flow chemistry and solid phase synthesis, have also emerged in the literature.

Entities:  

Keywords:  Bis(trichloromethyl) carbonate; Carbonyl compounds; Heterocycles; Organohalides; Triphosgene

Year:  2020        PMID: 33883783      PMCID: PMC8054975          DOI: 10.1016/j.tet.2020.131553

Source DB:  PubMed          Journal:  Tetrahedron        ISSN: 0040-4020            Impact factor:   2.457


  35 in total

1.  Continuous in situ generation and reaction of phosgene in a microflow system.

Authors:  Shinichiro Fuse; Nobutake Tanabe; Takashi Takahashi
Journal:  Chem Commun (Camb)       Date:  2011-10-31       Impact factor: 6.222

2.  Oriented synthesis and in vitro anticancer activity of biquinazoline-2,2'-diones.

Authors:  Guolan Dou; Daqing Shi; Yonghai Li
Journal:  J Comb Chem       Date:  2010 Jan-Feb

3.  Flow synthesis of ethyl isocyanoacetate enabling the telescoped synthesis of 1,2,4-triazoles and pyrrolo-[1,2-c]pyrimidines.

Authors:  Marcus Baumann; Antonio M Rodriguez Garcia; Ian R Baxendale
Journal:  Org Biomol Chem       Date:  2015-03-06       Impact factor: 3.876

4.  Efficient Synthesis and Stereochemical Revision of Coibamide A.

Authors:  Guiyang Yao; Zhengyin Pan; Chunlei Wu; Wei Wang; Lijing Fang; Wu Su
Journal:  J Am Chem Soc       Date:  2015-10-15       Impact factor: 15.419

5.  Ring strain-dictated divergent fluorinating Prins cyclization or semipinacol rearrangement.

Authors:  Yi Liu; Ying-Yeung Yeung
Journal:  Org Biomol Chem       Date:  2017-08-09       Impact factor: 3.876

6.  Chlorination of aliphatic primary alcohols via triphosgene-triethylamine activation.

Authors:  Caitlan E Ayala; Andres Villalpando; Alex L Nguyen; Gregory T McCandless; Rendy Kartika
Journal:  Org Lett       Date:  2012-07-10       Impact factor: 6.005

7.  Triphosgene-amine base promoted chlorination of unactivated aliphatic alcohols.

Authors:  Andrés Villalpando; Caitlan E Ayala; Christopher B Watson; Rendy Kartika
Journal:  J Org Chem       Date:  2013-03-29       Impact factor: 4.354

8.  Triphosgene-pyridine mediated stereoselective chlorination of acyclic aliphatic 1,3-diols.

Authors:  Andrés Villalpando; Mirza A Saputra; Thomas H Tugwell; Rendy Kartika
Journal:  Chem Commun (Camb)       Date:  2015-10-18       Impact factor: 6.222

9.  Efficient amide bond formation through a rapid and strong activation of carboxylic acids in a microflow reactor.

Authors:  Shinichiro Fuse; Yuto Mifune; Takashi Takahashi
Journal:  Angew Chem Int Ed Engl       Date:  2013-12-02       Impact factor: 15.336

10.  Quinolines from the cyclocondensation of isatoic anhydride with ethyl acetoacetate: preparation of ethyl 4-hydroxy-2-methylquinoline-3-carboxylate and derivatives.

Authors:  Nicholas G Jentsch; Jared D Hume; Emily B Crull; Samer M Beauti; Amy H Pham; Julie A Pigza; Jacques J Kessl; Matthew G Donahue
Journal:  Beilstein J Org Chem       Date:  2018-09-28       Impact factor: 2.544

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  1 in total

1.  An amino-substituted 2-(2'-hydroxyphenyl)benzimidazole for the fluorescent detection of phosgene based on an ESIPT mechanism.

Authors:  Zi-Jie Li; Wen-Jie Zhang; Wen-Zhu Bi; Qiu-Juan Ma; Su-Xiang Feng; Xiao-Lan Chen; Ling-Bo Qu
Journal:  RSC Adv       Date:  2021-03-15       Impact factor: 3.361

  1 in total

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