Advances in Three-Component Coupling Reactions Involving CO2 DOI Open Access
Kun Xia,

Kaifa Zhang,

Sher Wali Khan

и другие.

Chinese Journal of Organic Chemistry, Год журнала: 2024, Номер 44(5), С. 1506 - 1506

Опубликована: Янв. 1, 2024

Carbon dioxide (CO2) is the attractive green and renewable C1 resource, its direct participation in organic synthesis reactions as a reaction feedstock or promoter, which research direction advocated by chemistry.On other hand, three-component coupling considered to be one of most strategies synthetic chemistry, capable synthesizing complex molecules directly from simple readily available raw materials.Based on this, this paper reviews systems involving CO2 material categorizes them according types products generated: carboxyl, ester, carbonyl, haloalkyl, cyano compounds well promoter.An outlook development such also given.Keywords carbon dioxide; chemistry; coupling; promoter 众所周知, 二氧化碳(CO 2 )是主要的温室气体之一, 全球 CO 的排放量巨大并且呈现逐年激增的态势 [1] .同 时, 也是地球上储量最丰富、廉价、无毒的气 体 [2][3][4] .从有机化学合成的角度来看, 可以作为合成 有机化合物的可再生 来源, 从环保、经济和可持续 发展的角度看, 这种 的应用策略相比传统的捕获和 存储 模式更具吸引力 [5][6] .利用 参与有机合成 反应, 通过形成 C-C 和 C-O 等化学键, 能够高效构筑 一系列具有良好生物活性的分子骨架和具有高附加价 值的功能材料等, 且这些有价值的有机化合物具有工业 生产的潜力 [7] .因此, 基于 这一 源的化学转化一 直备受关注, 目前为止也取得了很多研究成果: 例如, 通过 与光催化 [8] 、电催化 [9] 和连续流 [10] 等反应方式 的结合, 实现多种羧基化、羰基化等产物的合成; 对 C O 的 还 原 , 实 现化 合 物 烷 基化 、 氰 基 化的 转 化 [11][12] .另一方面, 多组分反应(MCR)是三种或多种反应物 反应生成单一产物的反应体系.MCR 为生成具有结构 多样性和分子复杂性的复杂分子提供了一种便捷的合 成途径.这些类型的反应具有原子效率高, 反应快速简 单, 省时省能等主要优点, 并且通常对环境友好.因此, MCR 在生物医学、有机合成和工业化学等各个研究领 域发挥着重要作用 [13] .在多组分反应中, 众所周知的人 名反应, Mannich 反应 [14] Strecker [15] Ugi [16]

Язык: Английский

Synthesis of 3-thiocyanated chromones via TCCA/NH4SCN-mediated cyclization/thiocyanation of alkynyl aryl ketones DOI Creative Commons
Jiaxi Xiao, Zhenkang Ai, Xuemin Li

и другие.

Green Synthesis and Catalysis, Год журнала: 2021, Номер 3(2), С. 198 - 201

Опубликована: Дек. 24, 2021

3-Thiocyanated chromones was conveniently synthesized from alkynyl aryl ketones using commercially available, inexpensive trichloroisocyanuric acid (TCCA) as oxidant and NH4SCN thiocyanato (SCN) source. This metal-free approach is postulated to first in situ generate thiocyanogen chloride (Cl-SCN) the reaction of TCCA NH4SCN, followed by a rare efficient electrophilic thiocyano oxyfunctionalization alkynes enabled reactive species generated thereof.

Язык: Английский

Процитировано

14

Insights into the chemistry and therapeutic potential of acrylonitrile derivatives DOI
Oya Ünsal Tan, Merve Zengin

Archiv der Pharmazie, Год журнала: 2021, Номер 355(3)

Опубликована: Ноя. 11, 2021

Abstract Acrylonitrile is a fascinating scaffold widely found in many natural products, drugs, and drug candidates with various biological activities. Several molecules such as entacapone, rilpivirine, teriflunomide, so forth, bearing an acrylonitrile moiety have been marketed. In this review, diverse synthetic strategies for constructing desired acrylonitriles are discussed, the different activities medicinal significance of derivatives critically evaluated. The information gathered expected to provide rational guidance development clinically useful agents from acrylonitriles.

Язык: Английский

Процитировано

13

Catalytic Hydrofunctionalization Reactions of 1,3-Diynes DOI Open Access
Victorio Cadierno

Catalysts, Год журнала: 2022, Номер 12(1), С. 89 - 89

Опубликована: Янв. 13, 2022

Metal-catalyzed hydrofunctionalization reactions of alkynes, i.e., the addition Y–H units (Y = heteroatom or carbon) across carbon–carbon triple bond, have attracted enormous attention for decades since they allow straightforward and atom-economic access to a wide variety functionalized olefins and, in its intramolecular version, relevant heterocyclic carbocyclic compounds. Despite conjugated 1,3-diynes being considered key building blocks synthetic organic chemistry, this particular class alkynes has been much less employed when compared terminal internal monoynes. The presence two C≡C bonds adds classical regio- stereocontrol issues associated with alkyne processes’ other problems, such as possibility undergo 1,2-, 3,4-, 1,4-monoadditions well double reactions, thus increasing number potential products that can be formed. In review article, metal-catalyzed these challenging substrates are comprehensively discussed.

Язык: Английский

Процитировано

9

Synthesis of Alkynyl Sulfides: Alkynyl Trifluoromethyl Sulfides and Thiocyanates DOI

Chunling Zeng,

Zhiwen Yuan,

Yinchun Jiao

и другие.

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(42)

Опубликована: Сен. 2, 2023

Abstract Sulfur‐containing alkynes, are important starting materials and intermediates in organic reactions. Some of sulfur‐containing alkynes display interesting bioactivities potentially applied as drugs. Various synthetic methodologies towards have been developed, including C(sp)−S coupling, thiolation, S ‐alkynylation, trifluoromethylthiolation, etc. In this review, the approaches alkynyl sulfides recent 3 years, well to form trifluoromethyl alkynylthiocyanates were highlighted. Firstly, property application introduced. After presenting superiority their methods classified presented details. According different kinds for sulfides, summarized proposed reaction mechanisms demonstrated if available.

Язык: Английский

Процитировано

4

Palladium-catalyzed bisthiolation of terminal alkynes for the assembly of diverse (Z)-1,2-bis(arylthio)alkene derivatives DOI Creative Commons
Yinlong Lai,

Shaoxi Yan,

Dan He

и другие.

RSC Advances, Год журнала: 2021, Номер 11(46), С. 28447 - 28451

Опубликована: Янв. 1, 2021

An efficient and straightforward palladium-catalyzed three-component cascade bisthiolation of terminal alkynes arylhydrazines with sodium thiosulfate (Na2S2O3) as the sulfur source for assembly functionalized (Z)-1,2-bis(arylthio)alkene derivatives is described. Using 0.5 mol% IPr-Pd-Im-Cl2 catalyst, a wide range are well tolerated, thus producing desired products in good yields functional group tolerance excellent regioselectivity. Moreover, this protocol could be readily scaled up, showing potential applications organic synthesis material science.

Язык: Английский

Процитировано

9

Chemoselective Preparation of Alkynes from Vicinal and Geminal Dibromoalkenes DOI
Hisashi Okumura, Nurcahyo Iman Prakoso,

Tatsuya Morozumi

и другие.

Organic Letters, Год журнала: 2024, Номер 26(46), С. 9817 - 9821

Опубликована: Ноя. 9, 2024

The reductive conversion of vicinal and geminal dibromoalkenes into the corresponding alkynes with

Язык: Английский

Процитировано

1

Recent Advances in the Synthesis of Organic Thiocyano (SCN) and Selenocyano (SeCN) Compounds, Their Chemical Transformations and Bioactivity DOI Creative Commons
Rodrigo Abonı́a, Daniel Insuasty, Juan‐Carlos Castillo

и другие.

Molecules, Год журнала: 2024, Номер 29(22), С. 5365 - 5365

Опубликована: Ноя. 14, 2024

New approaches for the synthesis of organic thio- and selenocyanates, methods to incorporate them into more complex structures, including a wide variety heterocyclic polycylic derivatives, are reviewed. Protocols that convert SCN SeCN moieties thio seleno derivatives by transforming cyano group also examined. In representative cases, bioactivity data these classes compounds

Язык: Английский

Процитировано

1

Zinc‐Catalyzed Hydrocyanation of Ynamides and Photoisomerization, a General and Selective Access to E and Z Trisubstituted α‐Enamidonitriles DOI Creative Commons

Pierre Hansjacob,

Frédéric R. Leroux, Morgan Donnard

и другие.

Chemistry - A European Journal, Год журнала: 2023, Номер 29(30)

Опубликована: Фев. 27, 2023

The fully regio- and stereoselective Zn-catalyzed hydrocyanation of ynamides is reported represents a general access to various trisubstituted E-α-enamidonitriles. catalyst-free photoisomerization selectively yields the energetically comparable Z-stereoisomer. Finally, synthetic potential these new α-enamidonitriles was evaluated through synthesis original heterocycles.

Язык: Английский

Процитировано

3

Construction of a Functionalized Selenophene‐Allylidene Ligand via Alkyne Double Action at a Diiron Complex DOI

Alice De Palo,

Stefano Zacchini, Guido Pampaloni

и другие.

European Journal of Inorganic Chemistry, Год журнала: 2020, Номер 2020(34), С. 3268 - 3276

Опубликована: Авг. 26, 2020

The diiron µ‐vinyliminium compounds [Fe 2 Cp (CO)(µ‐CO){µ‐η 1 :η 3 ‐C HC NMe(R)}]CF SO (R = Me, 2a ; R Xyl 2,6‐C 6 H Me , 2b η 5 ) reacted with grey selenium, in the presence of sodium methoxide, to give corresponding Se‐functionalized derivatives (Se)C NMe(R)}], 3a – b ca. 50 % yields. monoiron zwitterionic complex [FeCp(CO){SeC (NMe )C H}], 4 was obtained as a side‐product (31 %) reaction leading . treatment 3b S 8 /NaOMe afforded 2‐ferra‐thiophene [FeCp(CO){SC NMe(Xyl)}], 49 yield. straightforward reactions two‐fold excess dialkylacetylenedicarboxylates led functionalized 3‐amino‐selenophenes appended frame through bridging allylidene ligand, 7 (CO R)C SeC )}] 6a Et, 6b t Bu, 6c ), approximately synthesis c is result two distinct modes reactivity exhibited by alkyne reactant one pot, i.e. 1,3‐dipolar cycloaddition C and Se atoms insertion into Fe‐µ‐alkylidene. All products were characterized means elemental analysis, IR multinuclear NMR spectroscopy, molecular structure elucidated single‐crystal X‐ray diffraction study.

Язык: Английский

Процитировано

8

Electrophilic Oxythio/selenocyanation of o‐Alkenyl Benzoic Acids: Divergent Synthesis of Thio/selenocyanated Isobenzofuranones and Isocoumarins DOI

Shanqing Tao,

Luchen Jiang, Yunfei Du

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2022, Номер 11(12)

Опубликована: Ноя. 17, 2022

Abstract A transition‐metal free thio/selenocyanation of o ‐alkenyl benzoic acids via the electrophilic Cl−S(Se)CN species, in‐situ generated from inorganic thio/selenocyanating salt and PhICl 2 , has been realized under mild reaction conditions. This protocol offers a divergent synthesis thio/selenocyanated isobenzofuranones isocoumarins, depending on substitution type substrates.

Язык: Английский

Процитировано

4