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Intermediate Detection by SAESI-MS/MS Unveiling the Catalytic Cycle in Negishi Coupling

Chinese Journal of Chemistry 2020年第1期38卷 106-107页

作者： Yangguangyan Zheng bukeyan miao Li Zhang Department of Chemistry FudanUniversity220 Handan LuShanghai 200433China State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of Sciences345 Lingling LuShanghai 200032China

Becausecarbon dioxideisabundant,cheap andnontoxic in or-ganic synthesis,much work hasbeen done in organic synthesis with carbon dioxide.[1]Allenes are an important series of com-pounds,and there arelots of reports about synthesis of allenes or using allenes as starting materialsin recent years.[2]In our previ-ous work,we reportedthe synthesis of allenoic acids by using 2-alkynyl bromides with zinc powder under CO2atmosphere.[3]In order to synthesizeallenoic acids,at the beginning of our study,1-phenylhept-2-ynyl methyl carbonate 1aand diethyl zinc were used as the substrates for optimization of the reaction conditions under *** allenoic acid nor its zincate was obtained as we ***,a mixture of ethylation prod-uct 2aandβ-H elimination product 3awas formed instead as judged by NMR.β-H elimination is an intrinsic challenge in or-ganometallic reactions involving alkyl species.

关键词： synthesis dioxide elimination

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Negishi Coupling for Highly Selective Syntheses of Allenes via Ligand Effect and Mechanistic Study via SAESI-MS/MS

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Chinese Journal of Chemistry 2019年第10期37卷 1003-1008页

作者： Yangguangyan Zheng bukeyan miao Anni Qin Junzhe Xiao Qi Liu Gen Li Li Zhang Fang Zhang Yinlong Guo Shengming Ma Department of Chemistry Fudan University220 Handan LuShanghai 200433China State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of Sciences345 Lingling LuShanghai 200032China National Center for Organic Mass Spectrometry in Shanghai Shanghai Institute of Organic ChemistryChinese Academy of Sciences345 Lingling LuShanghai 200032China

β-H elimination is an intrinsic problem in transition metal-catalyzed *** describe herein an interesting ligand effect for Et2Zn acting as either ethyl provider or H provider,respectively:by applying SPhos or Gorlos-Phos as the ligand,β-H elimination has been successfully controlled in the corresponding Negishi coupling reaction affording different poly-substituted allenes in good yields and excellent ***-MS (Solvent Assisted Electrospray Ionization Mass Spectrometry) has been applied to successfully capture the highly reactive organometallic intermediates,which show the different coordination behaviors of Pd with SPhos or Gorlos-Phos as the ligand in the catalytic *** addition,the different reactivities of Int 1 and Int 2 towards the formation of the final allene products have been demonstrated via SAESI-MS/MS *** MS studies visualized the whole catalytic cycle for the Negishi coupling reaction while nicely explain the observed reactivity and selectivity.

关键词： elimination Highly substituted

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