Grignard Method for Preparing Thioesters from Esters and Its Application to One-Pot Synthesis of Ketones and Aldehydes

被引：0

作者：

Mulani, Shaheen K. ^{[1
]}

Kang, Jiaao ^{[1
]}

Yang, Runlin ^{[1
]}

Uchibayashi, Akinari ^{[1
]}

Arisawa, Mitsuhiro ^{[1
]}

Seki, Masahiko ^{[2
]}

Mashima, Kazushi ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Osaka 5650871, Japan

[2] Tokuyama Corp, R&D Planning Dept, Tsukuba 3004247, Japan

来源：

ACS OMEGA | 2025年 / 10卷 / 08期

基金：

日本学术振兴会;

关键词：

PALLADIUM-CATALYZED THIOCARBONYLATION; CARBON-MONOXIDE; ARYL HALIDES; THIOL ESTERS; THIOESTERIFICATION; EFFICIENT; OXYGEN; MILD; TRANSESTERIFICATION; ESTERIFICATION;

D O I：

10.1021/acsomega.4c10622

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new protocol for preparing thioesters from the corresponding methyl esters was developed using i PrMgCl and odorless 1-dodecanthiol, n C12H25SH, under mild reaction conditions, during which in situ-generated C12H25SMgCl selectively reacted with the carbonyl group of esters. A variety of aromatic and aliphatic esters were readily converted in up to 99% yield with excellent functional group tolerance. Furthermore, based on the quantitative formation of the thioesters, we successfully applied our method to a one-pot synthesis of ketones and aldehydes from esters.

引用

页码：8462 / 8471

页数：10

共 65 条

[21] FACILE ALKOXYL EXCHANGE OF 2-METHOXYBENZOATES VIA NUCLEOPHILIC AROMATIC-SUBSTITUTION WITH SODIUM ALKOXIDES IN DIMETHYLFORMAMIDE
HATTORI, T
SATOH, S
MIYANO, S
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1993, 66 (12) : 3840 - 3842
[22] Regioselective Thiocarbonylation of Vinyl Arenes
Hirschbeck, Vera
Gehrtz, Paul H.
Fleischer, Ivana
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (51) : 16794 - 16799
[23] Captopril as a nucleophile for ester cleavage. Formation of the thiolester S-benzoylcaptopril
Iglesias, Emilia
Brandariz, Isabel
[J]. RSC ADVANCES, 2015, 5 (57): : 45740 - 45748
[24] Hydrophobic polymer-supported catalyst for organic reactions in water: Acid-catalyzed hydrolysis of thioesters and transprotection of thiols
Iimura, S
Manabe, K
Kobayashi, S
[J]. ORGANIC LETTERS, 2003, 5 (02) : 101 - 103
[25] Data-Mining for Sulfur and Fluorine: An Evaluation of Pharmaceuticals To Reveal Opportunities for Drug Design and Discovery
Ilardi, Elizabeth A.
Vitaku, Edon
Njardarson, Jon T.
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (07) : 2832 - 2842
[26] In situ generated Ph3P(OAc)2 as a novel reagent for the efficient acetylation of alcohols and thiols at room temperature
Iranpoor, Nasser
Firouzabadi, Habib
Davan, Elham Etemadi
[J]. TETRAHEDRON LETTERS, 2013, 54 (14) : 1813 - 1816
[27] Polymer supported Pd catalyzed thioester synthesis via carbonylation of aryl halides under phosphine free conditions
Islam, Sk Manirul
Molla, Rostam Ali
Roy, Anupam Singha
Ghosh, Kajari
[J]. RSC ADVANCES, 2014, 4 (50) : 26181 - 26192
[28] Rare Earth Amide-Catalyzed Direct Thioesterification of Aldehydes with Thiols under Mild Conditions
Ismaeel, Nadia
Imran, Sajid
Zhu, Xuehua
Chen, Jue
Yuan, Dan
Yao, Yingming
[J]. ORGANIC LETTERS, 2023, 25 (48) : 8672 - 8676
[29] Diarylcuprates for Selective Syntheses of Multifunctionalized Ketones from Thioesters under Mild Conditions
Kato, Daiki
Murase, Tomoya
Talode, Jalindar
Nagae, Haruki
Tsurugi, Hayato
Seki, Masahiko
Mashima, Kazushi
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (26)
[30] Thioesters synthesis: recent adventures in the esterification of thiols
Kazemi, Mosstafa
Shiri, Lotfi
[J]. JOURNAL OF SULFUR CHEMISTRY, 2015, 36 (06) : 613 - 623

← 1 2 3 4 5 6 7 →