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Lewis Base Catalyzed Intramolecular Reduction of Salicylaldehydes by Pinacol‐Derived Chlorohydrosilane

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Lewis Base Catalyzed Intramolecular Reduction of Salicylaldehydes by Pinacol‐Derived Chlorohydrosilane. / Assoah, Benedicta; Vale, João R.; Kalenius, Elina; Veiros, Luis; Rafael Candeias, Nuno.

In: European Journal of Organic Chemistry, Vol. 2018, No. 23, 01.06.2018, p. 2910-2917.

Research output: Contribution to journalArticleScientificpeer-review

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Assoah, B, Vale, JR, Kalenius, E, Veiros, L & Rafael Candeias, N 2018, 'Lewis Base Catalyzed Intramolecular Reduction of Salicylaldehydes by Pinacol‐Derived Chlorohydrosilane', European Journal of Organic Chemistry, vol. 2018, no. 23, pp. 2910-2917. https://doi.org/10.1002/ejoc.201800544

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Author

Assoah, Benedicta ; Vale, João R. ; Kalenius, Elina ; Veiros, Luis ; Rafael Candeias, Nuno. / Lewis Base Catalyzed Intramolecular Reduction of Salicylaldehydes by Pinacol‐Derived Chlorohydrosilane. In: European Journal of Organic Chemistry. 2018 ; Vol. 2018, No. 23. pp. 2910-2917.

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@article{9d252f562f3f4c3f8ca441865bc13c72,
title = "Lewis Base Catalyzed Intramolecular Reduction of Salicylaldehydes by Pinacol‐Derived Chlorohydrosilane",
abstract = "A newly developed stable chlorohydrosilane derived from pinacol is herein described. This was successfully used in the reduction of salicylaldehydes in reasonable to excellent yields (51–97 {\%}). The ability of the hydrosilane to react as a reducing agent is increased upon the in situ formation of a trialkoxyhydrosilane and activation with a Lewis base, as further indicated by density functional theory studies. 1,3‐Dimethyl‐3,4,5,6‐tetrahydro‐2(1H)‐pyrimidinone (DMPU) was identified to be a suitable catalyst for this metal‐free reduction, promoting the regio‐ and chemoselective reduction of aldehydes in ortho‐position to phenols, despite the presence of vicinal ketones. The performance of pinacol‐derived chlorohydrosilane in the reduction of salicylaldehydes was further observed to be superior to that of well‐established commercially available chlorohydrosilanes.",
author = "Benedicta Assoah and Vale, {Jo{\~a}o R.} and Elina Kalenius and Luis Veiros and {Rafael Candeias}, Nuno",
year = "2018",
month = "6",
day = "1",
doi = "10.1002/ejoc.201800544",
language = "English",
volume = "2018",
pages = "2910--2917",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-VCH Verlag",
number = "23",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - Lewis Base Catalyzed Intramolecular Reduction of Salicylaldehydes by Pinacol‐Derived Chlorohydrosilane

AU - Assoah, Benedicta

AU - Vale, João R.

AU - Kalenius, Elina

AU - Veiros, Luis

AU - Rafael Candeias, Nuno

PY - 2018/6/1

Y1 - 2018/6/1

N2 - A newly developed stable chlorohydrosilane derived from pinacol is herein described. This was successfully used in the reduction of salicylaldehydes in reasonable to excellent yields (51–97 %). The ability of the hydrosilane to react as a reducing agent is increased upon the in situ formation of a trialkoxyhydrosilane and activation with a Lewis base, as further indicated by density functional theory studies. 1,3‐Dimethyl‐3,4,5,6‐tetrahydro‐2(1H)‐pyrimidinone (DMPU) was identified to be a suitable catalyst for this metal‐free reduction, promoting the regio‐ and chemoselective reduction of aldehydes in ortho‐position to phenols, despite the presence of vicinal ketones. The performance of pinacol‐derived chlorohydrosilane in the reduction of salicylaldehydes was further observed to be superior to that of well‐established commercially available chlorohydrosilanes.

AB - A newly developed stable chlorohydrosilane derived from pinacol is herein described. This was successfully used in the reduction of salicylaldehydes in reasonable to excellent yields (51–97 %). The ability of the hydrosilane to react as a reducing agent is increased upon the in situ formation of a trialkoxyhydrosilane and activation with a Lewis base, as further indicated by density functional theory studies. 1,3‐Dimethyl‐3,4,5,6‐tetrahydro‐2(1H)‐pyrimidinone (DMPU) was identified to be a suitable catalyst for this metal‐free reduction, promoting the regio‐ and chemoselective reduction of aldehydes in ortho‐position to phenols, despite the presence of vicinal ketones. The performance of pinacol‐derived chlorohydrosilane in the reduction of salicylaldehydes was further observed to be superior to that of well‐established commercially available chlorohydrosilanes.

U2 - 10.1002/ejoc.201800544

DO - 10.1002/ejoc.201800544

M3 - Article

VL - 2018

SP - 2910

EP - 2917

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 23

ER -