23725-23-7Relevant academic research and scientific papers
Triethylborane-Induced Hydrodehalogenation of Organic Halides by Tin Hydrides
Miura, Katsukiyo,Ichinose, Yoshifumi,Nozaki, Kyoko,Fugami, Keigo,Oshima, Koichiro,Utimoto, Kiitiro
, p. 143 - 147 (1989)
The reduction of organic halides with tributyltin hydride in the presence of a catalytic amount of triethylborane has been studied. (1) Alkyl iodides and alkyl bromides reacted easily with tin hydride at -78 deg C to give the corresponding hydrocarbons, while alkyl chlorides were sluggish to react and recovered unchanged. (2) The reduction of alkenyl halides such as 1-deuterio-1-iodo-1-dodecene and 1-iodo-1-triethylsilyl-1-dodecene proceeded nonstereospecifically. (3) The reduction of aryl halides with n-Bu3SnH-Et3B system was not so effective as the reduction of alkyl halides and alkenyl halides.Whereas aryl iodides were reduced at room temperature with n-Bu3SnH, aryl bromides hardly reacted with n-Bu3SnH even at 80 deg C.
An improved reductive demercuration of organomercurials using triethylborane
Kang, Sung Ho,Lee, Jung Hwa,Lee, Sung Bae
, p. 59 - 62 (2007/10/03)
Organomercurials, which were generated by intra- and inter-molecular mercury(II)-promoted electrophilic additions, have been reductively demercurated in situ efficiently using sodium borohydride in the presence of triethylborane at low temperature. Under these conditions, the frequently accompanying side reactions such as reductive elimination and oxidative demercuration have not been detected.
REACTION OF DITHIO-SUBSTITUTED CINNAMYLLITHIUM WITH CARBONYL COMPOUNDS: A TEST OF THE HSAB PRINCIPLE
Fang, Jim-Min,Chen, Ming-Yi,Yang, Wen-Jin
, p. 5937 - 5938 (2007/10/02)
By mediation of BF3.Et2O, dithio substituted cinnamyllithium 2 reacted predominantly at the α-site with carbonyl compounds.No selectivity was found when the reaction was performed in the absence of BF3.Et2O.
