2 research outputs found
Indium-Catalyzed Reductive Bromination of Carboxylic Acids Leading to Alkyl Bromides
The combination of 1,1,3,3-tetramethyldisiloxane (TMDS) and trimethylbromosilane (Me<sub>3</sub>SiBr) with a catalytic amount of indium bromide (InBr<sub>3</sub>) undertook direct bromination of carboxylic acids, which produced the corresponding alkyl bromides in good to excellent yields. The reducing system was tolerant to several functional groups
Indium(III)-Catalyzed Reductive Bromination and Iodination of Carboxylic Acids to Alkyl Bromides and Iodides: Scope, Mechanism, and One-Pot Transformation to Alkyl Halides and Amine Derivatives
Highly effective
indium(III)-catalyzed reductive bromination or
iodination of a variety of carboxylic acids with 1,1,3,3-tetramethyldisiloxane
(TMDS) and a source of bromine or iodine is described. This functional
group interconversion has high tolerance for several functional groups,
such as halogens, a hydroxy group, a nitro group, an olefin part,
and a sulfide moiety. This indium catalytic system is also applicable
to the reductive iodination of aldehyded, acyl chlorides, and esters.
Furthermore, this reducing system can be applied to the one-pot synthesis
of alkyl halides and amine derivatives via the addition of nucleophiles.
Insight into the reaction mechanism was gained via the time course
of <sup>1</sup>H and <sup>13</sup>C NMR monitoring experiments and
the corresponding stepwise reactions