Literature DB >> 22780451

Chlorination of aliphatic primary alcohols via triphosgene-triethylamine activation.

Caitlan E Ayala1, Andres Villalpando, Alex L Nguyen, Gregory T McCandless, Rendy Kartika.   

Abstract

Activation of primary aliphatic alcohols with triphosgene and triethylamine mixtures afforded either alkyl chloride or diethylcarbamate products, and the switch in selectivity appeared to be driven by sterics. The reaction conditions to achieve this highly useful transformation were unexceptionally mild and readily tolerated by a wide range of sensitive functionalities.

Entities:  

Year:  2012        PMID： 22780451     DOI： 10.1021/ol301520d

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  8 in total

1.  Discovery, Optimization, and Characterization of ML417: A Novel and Highly Selective D3 Dopamine Receptor Agonist.

Authors:  Amy E Moritz; R Benjamin Free; Warren S Weiner; Emmanuel O Akano; Disha Gandhi; Ara Abramyan; Thomas M Keck; Marc Ferrer; Xin Hu; Noel Southall; Joseph Steiner; Jeffrey Aubé; Lei Shi; Kevin J Frankowski; David R Sibley
Journal:  J Med Chem       Date:  2020-05-12       Impact factor: 7.446

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

Authors:  Moshood O Ganiu; Binod Nepal; Joshua P Van Houten; Rendy Kartika
Journal:  Tetrahedron       Date:  2020-09-06       Impact factor: 2.457

3.  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

4.  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

5.  Atom interaction propensities of oxygenated chemical functions in crystal packings.

Authors:  Christian Jelsch; Yvon Bibila Mayaya Bisseyou
Journal:  IUCrJ       Date:  2017-01-21       Impact factor: 4.769

6.  7-Substituted 2-Nitro-5,6-dihydroimidazo[2,1-b][1,3]oxazines: Novel Antitubercular Agents Lead to a New Preclinical Candidate for Visceral Leishmaniasis.

Authors:  Andrew M Thompson; Patrick D O'Connor; Andrew J Marshall; Vanessa Yardley; Louis Maes; Suman Gupta; Delphine Launay; Stephanie Braillard; Eric Chatelain; Scott G Franzblau; Baojie Wan; Yuehong Wang; Zhenkun Ma; Christopher B Cooper; William A Denny
Journal:  J Med Chem       Date:  2017-05-11       Impact factor: 7.446

7.  Total synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a double cyclization strategy.

Authors:  Tomoki Itoh; Yuusuke Chiba; Shunsuke Kawaguchi; Yuki Koitaya; Yuuma Yoneta; Koji Yamada; Takumi Abe
Journal:  RSC Adv       Date:  2019-04-03       Impact factor: 4.036

8.  Preparation of Thin-Film Composite Nanofiltration Membranes Doped with N- and Cl-Functionalized Graphene Oxide for Water Desalination.

Authors:  Francisco J García-Picazo; Sergio Pérez-Sicairos; Gustavo A Fimbres-Weihs; Shui W Lin; Moisés I Salazar-Gastélum; Balter Trujillo-Navarrete
Journal:  Polymers (Basel)       Date:  2021-05-18       Impact factor: 4.329
  8 in total

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