Base-Promoted Reactions of Organostibines with Alkynes and Organic Halides to Give Chalcogenated (Z)-Olefins and Ethers

被引：12

作者：

Le, Liyuan ^{[1
]}

Li, Shuangshuang ^{[1
]}

Zhang, Dejiang ^{[1
]}

Yin, Shuang-Feng ^{[1
]}

Kambe, Nobuaki ^{[2
]}

Qiu, Renhua ^{[1
]}

机构：

[1] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemo Biosensing & Chemometr, R China, Changsha 410082, Peoples R China

[2] Osaka Univ, Grad Sch Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 33期

关键词：

BOND FORMATION; CATALYZED THIOETHERIFICATION; C-S; ORGANOANTIMONY; SULFUR; DISULFIDES; THIOLATION; REACTIVITY; CHLORIDES; TE;

D O I：

10.1021/acs.orglett.2c02369

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, with air-stable chalcogenated stibines (Sb-ER) as organometallic chalcogenating reagents, we developed base-promoted (Z)-hydrochalcogenation of alkynes with DMSO/DMSO-d(6) as hydrogen/deuterium sources, giving chalcogenated (Z)-olefins in good yields and with excellent regioselectivity. These reagents, easily synthesized from halostibines with in situ generated [Zn(ER)(2)] at room temperature within a few minutes, could be also used in the base-promoted C(sp(3))-S(Se) cross-coupling with C(sp(3))-X and copper-catalyzed C(sp(2))-S(Se) cross-coupling with C(sp(2))-X (X = F, CI, Br, I) under mild conditions. This protocol could also be simply extended to organobismuth complexes (Bi-ER) with good functional tolerance.

引用

页码：6159 / 6164

页数：6

共 8 条

[1] Base-Promoted Stereoselective Hydrogenation of Ynamides with Sulfonyl Hydrazide to Give Z-Enamides
Zhao, Zemin
Tian, Qingyu
Chen, Yanhui
Wen, Si
Zhang, Yuqing
Cheng, Guolin
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (15): : 10407 - 10413
[2] Biaryl Formation via Base-Promoted Direct Coupling Reactions of Arenes with Aryl Halides
Iqbal, Muhammad Asif
Lu, Le
Mehmood, Hina
Hua, Ruimao
ACS OMEGA, 2021, 6 (24): : 15981 - 15987
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Paquette, LA
Vilotijevic, I
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ORGANIC LETTERS, 2003, 5 (04) : 463 - 466
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Bluemel, Marcus
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Harper, Jason B.
Enders, Dieter
Nguyen, Thanh V.
CHEMICAL COMMUNICATIONS, 2016, 52 (51) : 7958 - 7961
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LIN, LHC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (17) : 4527 - &
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ARKIVOC, 2010, : 118 - 137
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BULLETIN OF THE POLISH ACADEMY OF SCIENCES-CHEMISTRY, 1984, 32 (1-2): : 39 - 47
[8] MECHANISMS OF NUCLEOPHILIC SUBSTITUTION OF PROPARGYL AND ALLENYL HALIDES . BASE-PROMOTED REACTIONS OF 3-BROMO-3-METHYL-1-BUTYNE AND 1-BROM0-3-METHYL-1,2-BUTADIENE IN AQUEOUS ETHNAOL
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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (03) : 622 - +

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