One-Step Synthesis of Triphenylphosphonium Salts from (Het)arylmethyl Alcohols

One-Step Synthesis of Triphenylphosphonium Salts from (Het)arylmethyl Alcohols Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2021, Volume: 86, Number: 14, Pages: 9838-9846 Pages count : 9 DOI: 10.1021/acs.joc.1c00733

Authors

Chalikidi Petrakis N. ¹ , Magkoev Taimuraz T. ¹ , Gutnov Andrey V. ^2,1 , Demidov Oleg P. ³ , Uchuskin Maxim G. ⁴ , Trushkov Igor V. ^5,6 , Abaev Vladimir T. ^3,1

Affiliations

1	North-Ossetian State University, Vatutina st. 46, Vladikavkaz, 362025, Russian Federation
2	Chiroblock GmbH, Andresenstr. 1a, Wolfen, 06766, Germany
3	North Caucasus Federal University, Pushkin st. 1, Stavropol, 355009, Russian Federation
4	Perm State University, Bukireva st. 15, Perm, 614990, Russian Federation
5	D. Rogachev National Medical Research Center of Pediatric Hematology, Oncology and Immunology, Samory Mashela st. 1, Moscow, 117997, Russian Federation
6	N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky pr. 47, Moscow, 119334, Russian Federation

Two approaches for the synthesis of substituted phosphonium salts from easily available benzyl alcohols and their heterocyclic analogs have been developed. The developed protocols are complementary: the direct mixing of alcohol, trimethylsilyl bromide, and triphenylphosphine in 1,4-dioxane followed by heating at 80 °C was found to be more efficient for acid-sensitive substrates, such as salicyl or furfuryl alcohols as well as secondary benzyl alcohols, while a one-pot procedure including sequential addition of trimethylsilyl bromide and triphenylphosphine gave higher yields for benzyl alcohols bearing electroneutral or electron-withdrawing substituents.

Chalikidi P.N. , Magkoev T.T. , Gutnov A.V. , Demidov O.P. , Uchuskin M.G. , Trushkov I.V. , Abaev V.T.
One-Step Synthesis of Triphenylphosphonium Salts from (Het)arylmethyl Alcohols
Journal of Organic Chemistry. 2021. V.86. N14. P.9838-9846. DOI: 10.1021/acs.joc.1c00733 WOS Scopus OpenAlex

Web of science:	WOS:000674931400049
Scopus:	2-s2.0-85110957206
OpenAlex:	W3182992851

DB	Citing
OpenAlex	5
Scopus	5
Web of science	3