5056-00-8Relevant articles and documents
M -C2B10H11HgCl/AgOTf-Catalyzed Reaction for Reductive Deoxygenation
Yamasaki, Naoto,Kanno, Marina,Sakamoto, Kyohei,Kasai, Yusuke,Imagawa, Hiroshi,Yamamoto, Hirofumi
, p. 169 - 175 (2018/03/26)
A m -C2B10H11HgCl/AgOTf-catalyzed reaction of allyl silyl ethers with N -Boc- N ′-tosylhydrazine has been developed. Under mild conditions, the resulting allyl hydrazine products were transformed into naked alkenes in good yield. Furthermore, the used m -C2B10H11HgCl could be recovered quantitatively.
Radical chain reduction of alkylboron compounds with catechols
Villa, Giorgio,Povie, Guillaume,Renaud, Philippe
, p. 5913 - 5920 (2011/06/16)
The conversion of alkylboranes to the corresponding alkanes is classically per-formed via protonolysis of alkylboranes. This simple reaction requires the use of severe reaction conditions, that is, treatment with a carboxylic acid at high temperature (>150 °C). We report here a mild radical procedure for the transformation of organoboranes to alkanes. 4-tert-Butylcatechol, a well-established radical inhibitor and antioxidant, is acting as a source of hydrogen atoms. An efficient chain reaction is observed due to the exceptional reactivity of phenoxyl radicals toward alkylboranes. The reaction has been applied to a wide range of organoboron derivatives such as B- alkylcatecholboranes, trialkylboranes, pinacolboronates, and alkylboronic acids. Furthermore, the so far elusive rate constants for the hydrogen transfer between secondary alkyl radical and catechol derivatives have been experimentally determined. Interestingly, they are less than 1 order of magnitude slower than that of tin hydride at 80 °C, making catechols particularly attractive for a wide range of transformations involving C-C bond formation.
Copper-Mediated and -Catalyzed o-DPPB-Directed Allylic Substitution
Breit, Bernhard,Demel, Peter
, p. 429 - 432 (2007/10/03)
Complete control of chemo-, regio- and stereoselectivity in the course of copper-catalyzed and -mediated allylic substitution could be obtained with me ortho-diphenylphosphanyl (o-DPPB) function as a reagent-directing leaving group. Complete chirality transfer by way of a syn-addition process has been achieved for cyclic and acyclic systems. Readily available Grignard reagents may be employed as nucleophiles and the directing o-DPPB group can be recovered quantitatively. The reaction requires neither cooling nor an excess of organometallic reagent.