Convenient Method for the Preparation of the 2-Methyl Thiophen-3-yl Magnesium Bromide Lithium Chloride Complex and Its Application to the Synthesis of 3-Substituted 2-Methylthiophenes

A series of butadienyl organomagnesium complexes, including 1-Li-4-(MgR)-butadienes, 1,4-bis(MgR)-butadienes, and 1-Mg-4-(MgR)-butadiene were synthesized starting with 1,4-dilithio butadienes via the transmetalation reaction between alkenyllithium bond and alkenylmagnesium bond. Single-crystal X-ray structural analysis of these butadienyl organomagnesiates revealed unique bonding modes. Study on their structural transformation demonstrated that 1-Li-4-(MgR)-butadiene is the key intermediate in the reaction process leading to the formation of 1,4-bis(MgR)-butadiene and 1-Mg-4-(MgR)-butadiene.

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Selective Transformation of Well‐Defined Alkenyllithiums to Alkenylmagnesiums via Transmetalation

Zhu

Liu

Zhang

et al. 2018

Chemistry A European J

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ChemInform Abstract: Convenient Method for the Preparation of the 2‐Methyl Thiophen‐3‐yl Magnesium Bromide Lithium Chloride Complex and Its Application to the Synthesis of 3‐Substituted 2‐Methylthiophenes.

Kogami

Watanabe

2013

ChemInform

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Convenient Method for the Preparation of the 2-Methyl Thiophen-3-yl Magnesium Bromide Lithium Chloride Complex and Its Application to theSynthesis of 3-Substituted 2-Methylthiophenes. -LiCl significantly accelerates the formation of Grignard reagent from inactive 3-bromo-2-methylthiophene (I) and thus provides access to a variety of 3-substituted 2-methylthiophenes (15 examples). -(KOGAMI, M.; WATANABE*, N.; Synth. Commun. 43 (2013) 5, 681-688, http://dx.

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Amplified Light-Induced pK_a Modulation with Diarylethene Photoswitches

Villabona,

Marco,

Sebastián

et al. 2024

J. Org. Chem.

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The reversible modulation of acidity using molecular photoswitches enables the remote control of a variety of (bio)chemical processes with light. Herein we investigated the structural features that allow amplifying photoinduced pK a variation in phenol-diarylethene conjugates, which toggle between low-and high-acidity states by switching the conjugation between the ionizable moiety and electronwithdrawing groups upon photoisomerization. By tuning the structure of these conjugates, high pK a modulation amplitudes were accomplished that surpass those previously reported.

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Convenient Method for the Preparation of the 2-Methyl Thiophen-3-yl Magnesium Bromide Lithium Chloride Complex and Its Application to the Synthesis of 3-Substituted 2-Methylthiophenes

Cited by 4 publications

References 3 publications

Selective Transformation of Well‐Defined Alkenyllithiums to Alkenylmagnesiums via Transmetalation

Selective Transformation of Well‐Defined Alkenyllithiums to Alkenylmagnesiums via Transmetalation

ChemInform Abstract: Convenient Method for the Preparation of the 2‐Methyl Thiophen‐3‐yl Magnesium Bromide Lithium Chloride Complex and Its Application to the Synthesis of 3‐Substituted 2‐Methylthiophenes.

Amplified Light-Induced pK_a Modulation with Diarylethene Photoswitches

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Convenient Method for the Preparation of the 2-Methyl Thiophen-3-yl Magnesium Bromide Lithium Chloride Complex and Its Application to the Synthesis of 3-Substituted 2-Methylthiophenes

Cited by 4 publications

References 3 publications

Selective Transformation of Well‐Defined Alkenyllithiums to Alkenylmagnesiums via Transmetalation

Selective Transformation of Well‐Defined Alkenyllithiums to Alkenylmagnesiums via Transmetalation

ChemInform Abstract: Convenient Method for the Preparation of the 2‐Methyl Thiophen‐3‐yl Magnesium Bromide Lithium Chloride Complex and Its Application to the Synthesis of 3‐Substituted 2‐Methylthiophenes.

Amplified Light-Induced pKa Modulation with Diarylethene Photoswitches

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Resources

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Amplified Light-Induced pK_a Modulation with Diarylethene Photoswitches