116384-68-0Relevant articles and documents
A Mechanochemical Zinc-Mediated Barbier-Type Allylation Reaction under Ball-Milling Conditions
Yin, JieXiang,Stark, Roderick T.,Fallis, Ian A.,Browne, Duncan L.
, p. 2347 - 2354 (2020/02/04)
A ball-milling-enabled zinc-mediated Barbier-type allylation reaction is reported. Notably, running the reaction in this manner renders it effective irrespective of the initial morphology of the zinc metal. The process is operationally simple, does not re
Substitution controlled functionalization of ortho -bromobenzylic alcohols via palladium catalysis: Synthesis of chromenes and indenols
Mahendar, Lodi,Satyanarayana, Gedu
supporting information, p. 2059 - 2074 (2014/04/03)
An efficient domino Pd-catalyzed transformation of simple ortho-bromobenzyl tertiary alcohols to chromenes is presented. Their formation is believed to proceed via the formation of a five-membered palladacycle, which, in turn, involves in an intermolecular homocoupling with the second ortho- bromobenzyltertiary alcohol to yield the homo-biaryl bond followed by intramolecular C-O bond formation. Interestingly, when there is an allylic substituent on the benzylic carbon atom, a chemoselective switch was observed, which preferred intramolecular Heck coupling and gave indenols. Further, it has been confirmed that the tertiary alcohol functionality is indispensible to give the coupled products, whereas the use of primary/secondary benzylic alcohols furnished the simple carbonyl products via a possible reductive debromination followed by oxidation due to the availability of β-hydrogen(s).
The mechanism and an improved asymmetric allylboration of ketones catalyzed by chiral biphenols
Barnett, David S.,Moquist, Philip N.,Schaus, Scott E.
supporting information; experimental part, p. 8679 - 8682 (2010/02/28)
Giving it a boost: A mechanistic study of the enantioselective asymmetric titled reaction with allyldiisopropoxyborane catalyzed by chiral biphenols revealed a key ligand exchange process which liberates isopropyl alcohol. The addition of iPrOH to the rea
Catalytic use of indium(0) for carbon-carbon bond transformations in water: General catalytic allylations of ketones with allylboronates
Schneider, Uwe,Ueno, Masaharu,Kobayashi, Shu
supporting information; experimental part, p. 13824 - 13825 (2009/02/07)
We have discovered the unprecedented catalytic use of In(0) for catalytic C-C bond transformations. Remarkably, these general catalytic allylations of ketones proceeded smoothly in water as a sole solvent under mild conditions, and water proved to be essential for these reactions. Both the displayed substrate scope and the functional group tolerance were excellent. Importantly, the In metal catalyst could be easily recovered and reused without loss of catalytic activity. Moreover, when an α-substituted allylboronate was used, an unusual constitutional selectivity was observed providing exclusively the formal α-adduct. Additionally, the resulting tertiary homoallylic alcohols were obtained with exceptionally high diastereoselectivities. The applicability of this concept to asymmetric catalysis in water by using In(0) combined with a chiral bis(oxazoline) ligand was demonstrated as well. Copyright
Catalytic activation of pinacolyl allylboronate with indium(I): Development of a general catalytic allylboration of ketones
Schneider, Uwe,Kobayashi, Shu
, p. 5909 - 5912 (2008/04/05)
(Chemical Equation Presented) Have to B In it to win it! The unprecedented catalytic activation of a Group 13 metal reagent (boron) with a Group 13 metal catalyst in its low oxidation state (indium) was employed for the development of a general catalytic
SnCl2-mediated carbonyl allylation of aldehydes and ketones in ionic liquid
Tang, Long,Ding, Li,Chang, Wei-Xing,Li, Jing
, p. 303 - 306 (2007/10/03)
In ionic liquid [bmim]BF4, SnCl2·2H 2O acts as an inexpensive and efficient metal salt for carbonyl allylation. By applying ionic liquid, some previously reported serious operational problems associated with the SnCl2-mediated allylation reaction are avoided. Furthermore, ketones, which are less reactive than aldehydes, can also be allylated in high yields with this system.
The Total Synthesis of (+/-)-cis- and trans-Trikentrin A
MacLeod, John K.,Monahan, Lilian C.
, p. 329 - 337 (2007/10/02)
The synthesis of the title compounds, which are novel cyclopentindoles isolated from a marine sponge Trikentrion flabelliforme, is described.An aryl radical cyclization and a 1,5-electrocyclic reaction of a nitrene are key steps in formation of the two
THE SYNTHESIS OF (+/-)CIS-TRIKENTRINA
Macleod, John K.,Monahan, Lilian C.
, p. 391 - 392 (2007/10/02)
The synthesis of a novel sponge metabolite is described, utilising an aryl radical cyclisation to form the substituted indane system.
