Literature DB >> 22272578

Electron transfer reduction of carboxylic acids using SmI2-H2O-Et3N.

Michal Szostak1, Malcolm Spain, David J Procter.   

Abstract

The first general method for efficient electron transfer reduction of carboxylic acids has been developed. The protocol using SmI(2)-H(2)O-Et(3)N allows for reduction of a variety of carboxylic acids in excellent yields and provides an attractive alternative to processes mediated by reactive alkali metals, lithium aluminum hydride, and boron hydrides. Of broader significance, the method allows acyl radical equivalents to be generated from carboxylic acids under mild reaction conditions.
© 2012 American Chemical Society

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Year:  2012        PMID: 22272578     DOI: 10.1021/ol203361k

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


  8 in total

1.  Reduction of liquid terminated-carboxyl fluoroelastomers using NaBH4/SmCl3.

Authors:  Yunfei Chang; Mingyi Liao; Xueyan Li
Journal:  RSC Adv       Date:  2020-03-17       Impact factor: 3.361

2.  On the role of pre- and post-electron-transfer steps in the SmI2 /amine/H(2)O-mediated reduction of esters: new mechanistic insights and kinetic studies.

Authors:  Michal Szostak; Malcolm Spain; David J Procter
Journal:  Chemistry       Date:  2014-03-11       Impact factor: 5.236

3.  Selective reduction of barbituric acids using SmI2/H2O: synthesis, reactivity, and structural analysis of tetrahedral adducts.

Authors:  Michal Szostak; Brice Sautier; Malcolm Spain; Maike Behlendorf; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-09       Impact factor: 15.336

4.  Uncovering the importance of proton donors in TmI2-promoted electron transfer: facile C-N bond cleavage in unactivated amides.

Authors:  Michal Szostak; Malcolm Spain; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-12       Impact factor: 15.336

5.  Samarium Iodide Showcase: Unraveling the Mechanistic Puzzle.

Authors:  Shmaryahu Hoz
Journal:  Acc Chem Res       Date:  2020-10-16       Impact factor: 22.384

6.  Formal total synthesis of histrionicotoxin alkaloids via Hg(OTf)2-catalyzed cycloisomerization and SmI2-induced ring expansion.

Authors:  Kunihiro Matsumura; Keisuke Nishikawa; Hiroaki Yoshida; Matsumi Doe; Yoshiki Morimoto
Journal:  RSC Adv       Date:  2018-03-21       Impact factor: 3.361

7.  Development of an additive-controlled, SmI2-mediated stereoselective sequence: Telescoped spirocyclisation, lactone reduction and Peterson elimination.

Authors:  Brice Sautier; Karl D Collins; David J Procter
Journal:  Beilstein J Org Chem       Date:  2013-07-18       Impact factor: 2.883

8.  Highly chemoselective reduction of amides (primary, secondary, tertiary) to alcohols using SmI2/amine/H2O under mild conditions.

Authors:  Michal Szostak; Malcolm Spain; Andrew J Eberhart; David J Procter
Journal:  J Am Chem Soc       Date:  2014-01-31       Impact factor: 15.419

  8 in total

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