280561-94-6

Upstream product

• 100-52-7 benzaldehyde 
• 257887-58-4 (3-bromo-3, 3-difluoroprop-1-yn-1-yl)triisopropylsilane 

Downstream Products

• 916332-95-1 3,3-difluoro-4-phenyl-4-(2-propynyloxy)-1-butyne 

Relevant academic research and scientific papers

On the nature of organoindium intermediates: The formation of readily isolable difluoropropargylindium reagents and their regioselectivity towards electrophilic substitutions

The structure and reactivity of intermediate propargylindium complexes have been investigated. Their reaction with electrophiles produced a difluoroalkyne or -allene, depending on the nature of the electrophiles. A mechanism based on the Curtin-Hammett principle was invoked to explain this phenomenon. A newly proposed mechanism on the formation of indium(III) complexes, through the intermediacy of indium(I) species, could help to explain the reaction of indium with 1,1,1-difluorobromo-2-alkynes in the presence of aldehydes.

Fluorinated Building Blocks. the Discovery of a Stable Difluoroallenyl Indium and the Synthesis of gem-Difluoroallenyl and -propargyl Synthons in Aqueous Media

The synthesis of two highly functional fluorinated motifs, TIPS-C≡C-CF2-, and CF2=C=C(TIPS)-is described. This approach is mediated by a room-temperature stable ethereal solution of a difluoroallene indium intermediate. This intermediate may be used as stock solution in the reaction with aqueous HCHO, to yield CF2=C=C(TIPS)CH2OH, and in a reaction with a Schiff base to produce the corresponding β,β-difluorohomopropargylamine. The synthetic potential of CF2=C=C(TIPS)CH2-OH has been demonstrated by its conversion to a difluorodihydrofuran derivative by a facile and efficient 5-endo-trig cyclization. Homopropargylic gem-difluoro alcohols are synthesized by addition of indium to a mixture of an aldehyde and TIPS-C≡C-CF2Br in predominantly aqueous media.

Crystallographic characterization of difluoropropargyl indium bromide, a reactive fluoroorganometallic reagent

Elusive intermediate trapped: γ-Substituted difluoropropargyl groups can stabilize an organoindium(III) complex. The resulting structure is the only known example of an indium atom bonded to a propargylic carbon atom (see picture; F blue, S yellow, C white, H green). Reactions with electrophiles produced a difluoroalkyne or -allene, depending on the type of electrophile. (Chemical Equation Presented).

Lanthanide triflate-catalyzed preparation of β,β- difluorohomopropargyl alcohols in aqueous media. Application to the synthesis of 4,4-difluoroisochromans

An indium-mediated Barbier-type reaction of difluoropropargyl bromide with several aldehydes in aqueous media was enhanced by a catalytic amount of a lanthanide triflate (5 mol %). The reaction gave the corresponding β,β-difluorohomopropargyl alcohols wit

Expedient synthesis of α,α-difluorohomopropargylic alcohols from TIPS- difluorobromopropyne via a Zn-mediated propargylation of aldehydes and ketones

The synthesis of α,α-difluorohomopropargyl alcohols containing an alkynyl silane moiety is reported. The title compound was prepared by the reaction of the organozinc derivative of TIPS-bromodifluoropropyne with aldehydes or ketones under mild conditions and in good yields. (C) 2000 Elsevier Science Ltd.