20605-48-5Relevant academic research and scientific papers
1,1,1,3,3,3-Hexafluoro-2-propanol (HFIP)-Assisted Catalyst-Free Sulfonation of Allylic Alcohols with Sulfinyl Amides
Hong, Chuan-Ming,Li, Qing-Hua,Liu, Tang-Lin,Liu, Zheng-Qiang,Luo, Zhen,Xue, Zhi-Yong,Yang, Ting-Ting,Zhuang, Xin,Zou, Fei-Fei
supporting information, p. 741 - 745 (2022/01/28)
A highly regioselective and catalyst-free sulfonation of allylic alcohols with sulfinyl amides has been realized. Such a mix-and-go procedure provides a convenient approach to synthetically various allylic sulfones under mild reaction conditions. Furthermore, this novel reaction shows ample substrate scope and outstanding functional group tolerance and could also be scaled-up. Meanwhile, it is the first example that sulfinyl amides act as a powerful sulfur nucleophile in the reactions. 1,1,1,3,3,3-Hexafluoro-2-propanol (HFIP) as a solvent plays a critical role in allylic sulfonation.
Visible-Light-Catalyzed in Situ Denitrogenative Sulfonylation of Sulfonylhydrazones
Huang, Xiang,Chen, Xing,Xie, Haisheng,Tan, Zheng,Jiang, Huanfeng,Zeng, Wei
, p. 6784 - 6788 (2021/09/08)
A photocatalyzed in situ denitrogenative sulfonylation of N-arylsulfonyl hydrazones has been developed. This transformation provides a low-carbon strategy to assemble arylalkyl sulfones in a stepwise denitrogenation/sulfonylation manner.
Palladium-catalyzed substitution of allylic alcohols with sulfinate salts: A synthesis of bicalutamide
Jhang, Yin-Jia,Chang, Chieh-Yu,Lin, Yu-Huan,Lee, Chein-Chung,Wu, Yen-Ku
supporting information, (2021/05/04)
A method is presented for the direct substitution of allylic alcohols with sodium arylsulfinates. The process involves a cooperative action of palladium catalysts, phenylboronic acid and titanium tetraisopropoxide. By taking advantage of this protocol, we achieved a concise synthesis of bicalutamide, an anti-androgen compound for treating prostate cancer.
Water-Promoted Dehydrative Tsuji–Trost Reaction of Non-Derivatized Allylic Alcohols with Sulfinic Acids
Yu, Jing,Chang, Xueping,Ma, Ruitian,Zhou, Qiuju,Wei, Mengmeng,Cao, Xinhua,Ma, Xiantao
, p. 7238 - 7242 (2020/10/30)
A mild, green and extra activator-free synthesis of allylic sulfones from non-derivatized allylic alcohols and sulfinic acids was developed and only the easily-available Pd(PPh3)4 was used as the catalyst. This new method could be easily scaled up to gram scale, affording the target allylic sulfones in a nearly quantitative yield with water as the sole by-product. Mechanism studies both by various NMR techniques and by theoretical calculations suggested two reaction pathways may be involved in the reaction, which are dependent on the reaction media, that is, an eight-membered ring binding species may be formed in aqueous media between allylic alcohol, sulfinic acid and water, while a six-membered ring binding species may be formed in common aprotic organic solvent between allylic alcohol and sulfinic acid. Both binding species may be accounted for the efficient activation of allylic alcohols via hydrogen bonding.
Reciprocal-Activation Strategy for Allylic Sulfination with Unactivated Allylic Alcohols
Xie, Peizhong,Sun, Zuolian,Li, Shuangshuang,Cai, Xinying,Qiu, Ju,Fu, Weishan,Gao, Cuiqing,Wu, Shisheng,Yang, Xiaobo,Loh, Teck-Peng,Loh, Teck-Peng
supporting information, p. 4893 - 4897 (2020/06/24)
A reciprocal-activation strategy for allylic sulfination with unactivated allylic alcohols was developed. In this reaction, the hydrogen bond interaction between allylic alcohols and sulfinic acids allowed for reciprocal activation, which enabled a dehydrative cross-coupling process to occur under mild reaction conditions. This reaction worked in an environmentally friendly manner, yielding water as the only byproduct. A variety of allylic sulfones could be obtained in good to excellent yields with wide functional group tolerance. In gram scale reactions, allylic sulfones could be conveniently isolated in high yield by filtration.
Synthetic method for allyl sulfone
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Paragraph 0042-0046, (2019/01/08)
The invention belongs to the field of organic synthesis, and especially relates to a synthetic method for allyl sulfone. The synthetic method for allyl sulfone is provided. Protonic acid can be simultaneously added as an additive under the catalysis of a
Visible Light-Induced Room-Temperature Heck Reaction of Functionalized Alkyl Halides with Vinyl Arenes/Heteroarenes
Kurandina, Daria,Parasram, Marvin,Gevorgyan, Vladimir
supporting information, p. 14212 - 14216 (2017/10/13)
The first visible light-induced Pd-catalyzed Heck reaction of α-heteroatom substituted alkyl iodides and -bromides with vinyl arenes/heteroarenes has been developed. This transformation efficiently proceeds at room temperature and enables synthesis of valuable functionalized allylic systems, such as allylic silanes, boronates, germanes, stannanes, pivalates, phosphonates, phthalimides, and tosylates from the corresponding α-substituted methyl iodides. Notably, synthesis of the latter substrates failed under existing thermally induced Pd-catalyzed conditions, which highlights the importance of visible light for this transformation.
Palladium-catalyzed allylation of sulfonyl hydrazides with alkynes to synthesize allylic arylsulfones
Lu, Chuan-Jun,Chen, Hong,Chen, Dong-Kai,Wang, Hong,Yang, Zhen-Ping,Gao, Jianrong,Jin, Hongwei
, p. 10833 - 10839 (2016/12/06)
A novel method for the construction of allyl arylsulfone derivatives was developed by palladium catalyzed allylation of sulfonyl hydrazides with alkynes. A series of structurally diverse allyl arylsulfones can be regioselectively synthesized in high yields under mild conditions.
Base-promoted coupling of carbon dioxide, amines, and N-tosylhydrazones: A novel and versatile approach to carbamates
Xiong, Wenfang,Qi, Chaorong,He, Haitao,Ouyang, Lu,Zhang, Min,Jiang, Huanfeng
supporting information, p. 3084 - 3087 (2015/05/12)
A base-promoted three-component coupling of carbon dioxide, amines, and N-tosylhydrazones has been developed. The reaction is suggested to proceed via a carbocation intermediate and constitutes an efficient and versatile approach for the synthesis of a wide range of organic carbamates. The advantages of this method include the use of readily available substrates, excellent functional group tolerance, wide substrate scope, and a facile work-up procedure.
One-pot synthesis of substituted tetrahydrocyclobuta[a]naphthalenes by domino aldol condensation/olefin migration/electrocyclization
Chang, Meng-Yang,Wu, Ming-Hao,Chen, Yeh-Long
supporting information, p. 2822 - 2825 (2013/07/26)
A facile one-pot synthetic route for preparing the novel benzofused tricyclic skeleton of 1,2,2a,8b-tetrahydrocyclobuta[a]naphthalenes 5 is developed. The route was realized by a NaH-mediated tandem aldol condensation/olefin migration/electrocyclization of o-allylbenzaldehydes 1 with cinnamyl sulfones 3 in good yields.
