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12. Zinc Promoted Cross‐Electrophile Sulfonylation to Access Alkyl–Alkyl Sulfones.

Author

Wang, Zhuochen, Ma, Rui, Gu, Chang, He, Xiaoqian, Shi, Haiwei, Bai, Ruopeng, and Shi, Renyi

Subjects
TRANSITION metal catalysts, HALOALKANES, ELECTROPHILES, CHARGE exchange, ZINC, SULFONES
Abstract

The transition metal‐catalyzed multi‐component cross‐electrophile sulfonylation, which incorporates SO2 as a linker within organic frameworks, has proven to be a powerful, efficient, and cost‐effective means of synthesizing challenging alkyl–alkyl sulfones. Transition metal catalysts play a crucial role in this method by transferring electrons from reductants to electrophilic organohalides, thereby causing undesirable side reactions such as homocoupling, protodehalogenation, β‐hydride elimination, etc. It is worth noting that tertiary alkyl halides have rarely been demonstrated to be compatible with current methods owing to various undesired side reactions. In this work, a zinc‐promoted cross‐electrophile sulfonylation is developed through a radical‐polar crossover pathway. This approach enables the synthesis of various alkyl–alkyl sulfones, including 1°‐1°, 2°‐1°, 3°‐1°, 2°‐2°, and 3°‐2° types, from inexpensive and readily available alkyl halides. Various functional groups are well tolerated in the work, resulting in yields of up to 93%. Additionally, this protocol has been successfully applied to intramolecular sulfonylation and homo‐sulfonylation reactions. The insights gained from this work shall be useful for the further development of cross‐electrophile sulfonylation to access alkyl–alkyl sulfones. [ABSTRACT FROM AUTHOR]

Published
2024
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15. Rhodium-Catalyzed Direct ortho-Arylation of Anilines

Author

Jacob, Clément, Annibaletto, Julien, Peng, Ju, Bai, Ruopeng, Maes, Bert U. W., Lan, Yu, Evano, Gwilherm, Jacob, Clément, Annibaletto, Julien, Peng, Ju, Bai, Ruopeng, Maes, Bert U. W., Lan, Yu, and Evano, Gwilherm

Abstract

An efficient and broadly applicable rhodium-catalyzed direct ortho-arylation of anilines with aryl iodides relying on readily available aminophosphines as traceless directing groups is reported. Its scope and functional group compatibility were both found to be quite broad as a large variety of both aminophosphines and (hetero)aryl iodides, including complex ones, could be utilized. The ortho-arylated anilines could be obtained in high average yields, without any competing diarylation and with full regioselectivity, which constitutes a major step forward compared to other processes. The reaction is moreover not limited to aryl iodides, as an aryl bromide and a triflate could be successfully used, and could be extended to diarylation. Mechanistic studies revealed the key and unique role of the aminophosphine, acting not only as a substrate but also as a ligand for the rhodium catalyst., SCOPUS: ar.j, info:eu-repo/semantics/published

Published
2024

49. Regiospecific construction of m-alkenyl benzaldehyde from β-bromoenal and vinyl borate.

Author

Xin, Xiaolan, Liu, Yilin, Zhou, Lu, Li, You, Luo, Han, Liu, Lei, Bai, Ruopeng, Lan, Yu, and Li, Baosheng

Subjects
BORATES, OPTICAL materials, BENZALDEHYDE, ESTERS
Abstract

Herein, we report a Pd-catalyzed regiospecific cycloaromatization of β-bromoenal and vinyl borate esters to synthesize m-alkenyl substituted benzaldehydes. This allows the construction of complex molecules from simple materials, which may be useful in the search for new optical materials. [ABSTRACT FROM AUTHOR]

Published
2022
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