Simple Preparation of 1-Bromo-1-Trimethylsilyl-1(Z), 4-pentadiene and its Use as 4-Pentenoyl Anion Equivalent

Yamaguchi, Ryohei; Kawasaki, H.; Kawanisi, Mituyosi

doi:10.1080/00397918208061944

Cited by 23 publications

(2 citation statements)

References 15 publications

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“…The Z-olefin geometry was affirmed by 1 H-1 H 2D NOSEY spectra of 3l ( Figure 2). Epoxidation of 3 with m-chloroperbenzoic acid occurred at the vinyl silanes to give epoxides 4, which were treated with trifluoroacetic acid in refluxing methanol to afford 5 in good yields 12 (Scheme 2 and Table 2).…”

Section: Methodsmentioning

confidence: 99%

Stereoselective Preparation of (Z)-γ-Silyl-γ,δ-Unsaturated Ketones and their Application in the Synthesis of 1,4-Diketones

Zheng¹,

Huang²

2002

Synthesis

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Section: Methodsmentioning

confidence: 99%

Stereoselective Preparation of (Z)-γ-Silyl-γ,δ-Unsaturated Ketones and their Application in the Synthesis of 1,4-Diketones

Zheng¹,

Huang²

2002

Synthesis

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“…A similar reaction was reported by Kawanisi and co-workers in 1980 which involved the use of ethynyltrimethylsilane and allyl bromide leading to geminally substituted silylated vinyl bromides 232 (Scheme 174). 317 These methods were extended to the one-pot Pd(II)-catalyzed alkyne-Suzuki 318 and -Wacker Oxidation/Sonogoashira 319 processes by Thadani and Rawal in 2002.…”

Section: Carbohalogenation Of Alkynes By Halometalationmentioning

confidence: 99%

Modern Transition-Metal-Catalyzed Carbon–Halogen Bond Formation

2016

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The high utility of halogenated organic compounds has prompted the development of a vast number of transformations which install the carbon-halogen motif. Traditional routes to these building blocks have commonly involved multiple steps, harsh reaction conditions, and the use of stoichiometric and/or toxic reagents. In this regard, using transition metals to catalyze the synthesis of organohalides has become a mature field in itself, and applying these technologies has allowed for a decrease in the production of waste, higher levels of regio- and stereoselectivity, and the ability to produce enantioenriched target compounds. Furthermore, transition metals offer the distinct advantage of possessing a diverse spectrum of mechanistic possibilities which translate to the capability to apply new substrate classes and afford novel and difficult-to-access structures. This Review provides comprehensive coverage of modern transition metal-catalyzed syntheses of organohalides via a diverse array of mechanisms. Attention is given to the seminal stoichiometric organometallic studies which led to the corresponding catalytic processes being realized. By breaking this field down into the synthesis of aryl, vinyl, and alkyl halides, it becomes clear which methods have surfaced as most favored for each individual class. In general, a pronounced shift toward the use of C-H bonds as key functional groups, in addition to methods which proceed by catalytic, radical-based mechanisms has occurred. Although always evolving, this field appears to be heading in the direction of using starting materials with a significantly lower degree of prefunctionalization in addition to less expensive and abundant metal catalysts.

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Bis(benzonitrile)dibromopalladium(II)

Lee¹

2001

Encyclopedia of Reagents for Organic Synthesis

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Simple Preparation of 1-Bromo-1-Trimethylsilyl-1(Z), 4-pentadiene and its Use as 4-Pentenoyl Anion Equivalent

Cited by 23 publications

References 15 publications

Stereoselective Preparation of (Z)-γ-Silyl-γ,δ-Unsaturated Ketones and their Application in the Synthesis of 1,4-Diketones

Stereoselective Preparation of (Z)-γ-Silyl-γ,δ-Unsaturated Ketones and their Application in the Synthesis of 1,4-Diketones

Modern Transition-Metal-Catalyzed Carbon–Halogen Bond Formation

Bis(benzonitrile)dibromopalladium(II)

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