A New Entry of Highly Selective and Nucleophilic BrH<sub>2</sub>C‐ and ClH<sub>2</sub>C‐Titanium Complexes for Carbonyl Coupling

Yan, Tu Hsin; Ananthan, Bakthavachalam; Chang, Suk-Joon

doi:10.1002/ejoc.201801438

Cited by 5 publications

(1 citation statement)

References 66 publications

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“…Another type of organometallic reagents was introduced by Yan and co-workers, applying dichloromethane and a mixture of TiCl 4 and metallic Mg for the formation of the chlorohydrins (Scheme 31). 33 In this investigation, aliphatic and aromatic aldehydes as well as ketones were tested and the desired products were obtained in good yields (Figure 15). However, more complex carbenoid-type reagents of the constitution Met-CHR-Cl seem not be applied thus far and represent an open field for future investigations.…”

Section: Scheme 30mentioning

confidence: 99%

The Synthetic Approaches to 1,2-Chlorohydrins

Hilt¹

2022

Synthesis

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This short review highlights the hitherto realised synthetic approaches towards organic 1,2-chlorohydrins by functionalisation of alkenes (i.e., 1,2-chlorohydroxylation), which is the most prominent access route to this class of compounds. Also, some other synthetic approaches involving the reduction of α-chloroketones, the epoxide opening ring by chloride anions and the utilisation of Grignard reagents for the synthesis of these compounds and chlorination of allylic alcohols are highlighted. Finally, enzymatic reactions for the formation of chlorohydrins are briefly summarised followed by a short view on natural products containing this moiety.1 Introduction2 Applications for the Synthesis of 1,2-Chlorohydrins2.1 Chlorohydroxylation of Alkenes2.2 Reduction of Chloroketones2.3 Metalorganic Reagents2.4 Epoxide Ring Opening2.5 Chlorination of Allylic Alcohols2.6 Biochemical Methods2.7 Selected Applications in Natural Product Total Synthesis3 Conclusion

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Section: Scheme 30mentioning

confidence: 99%

The Synthetic Approaches to 1,2-Chlorohydrins

Hilt¹

2022

Synthesis

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Straightforward synthesis of polycarbosilanes from chlorosilanes and chloromethanes by polycondensation using magnesium and titanium(IV) chloride

Fuchise

Takemoto

Satō

et al. 2021

European Polymer Journal

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Structure and Methylene Transfer Reactivity of Thiolate-Bridged Dichromium Methylene Complexes Derived from Dihalomethane via Cleavage of Two Carbon–Halogen Bonds

et al. 2021

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Using sterically demanding Cp′ (Cp′ = η 5 -1,2,4-t Bu 3 C 5 H 2 ) as auxiliary ligands, coordinatively unsaturated thiolate-bridged Cr II Cr II complexes were obtained by a facile salt metathesis strategy. This dichromium system with vacant coordination sites can easily cleave the two carbon−halogen bonds of dihalomethane by a cooperative activation effect. Meanwhile, it can accommodate the resulting methylene moiety and two halide groups. Notably, an unprecedented thiolate-bridged Cr III Cr III methylene complex was successfully isolated and unambiguously characterized by X-ray crystallography. Unlike the common chemical inertness of the {Cr−CH 2 −Cr} subunit, this bridging methylene fragment not only can interact with CH 2 Br 2 to give ethylene but can also transfer to styrene to generate the corresponding cyclopropanated product. In addition, the Cr III Cr III complex containing two halides can be easily reduced by mild Zn powder to regenerate the initial Cr II Cr II complex. Furthermore, this [Cr 2 S 2 ] reaction scaffold can catalyze the cyclopropanation of styrenes using CH 2 Br 2 as the methylene source.

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A New Entry of Highly Selective and Nucleophilic BrH₂C‐ and ClH₂C‐Titanium Complexes for Carbonyl Coupling

Cited by 5 publications

References 66 publications

The Synthetic Approaches to 1,2-Chlorohydrins

The Synthetic Approaches to 1,2-Chlorohydrins

Straightforward synthesis of polycarbosilanes from chlorosilanes and chloromethanes by polycondensation using magnesium and titanium(IV) chloride

Structure and Methylene Transfer Reactivity of Thiolate-Bridged Dichromium Methylene Complexes Derived from Dihalomethane via Cleavage of Two Carbon–Halogen Bonds

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A New Entry of Highly Selective and Nucleophilic BrH2C‐ and ClH2C‐Titanium Complexes for Carbonyl Coupling

Cited by 5 publications

References 66 publications

The Synthetic Approaches to 1,2-Chlorohydrins

The Synthetic Approaches to 1,2-Chlorohydrins

Straightforward synthesis of polycarbosilanes from chlorosilanes and chloromethanes by polycondensation using magnesium and titanium(IV) chloride

Structure and Methylene Transfer Reactivity of Thiolate-Bridged Dichromium Methylene Complexes Derived from Dihalomethane via Cleavage of Two Carbon–Halogen Bonds

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A New Entry of Highly Selective and Nucleophilic BrH₂C‐ and ClH₂C‐Titanium Complexes for Carbonyl Coupling