21438-74-4Relevant academic research and scientific papers
Umpolung Strategy for Arene C?H Etherification Leading to Functionalized Chromanes Enabled by I(III) N-Ligated Hypervalent Iodine Reagents
Mikhael, Myriam,Guo, Wentao,Tantillo, Dean J.,Wengryniuk, Sarah E.
supporting information, p. 4867 - 4875 (2021/09/14)
The direct formation of aryl C?O bonds via the intramolecular dehydrogenative coupling of a C?H bond and a pendant alcohol represents a powerful synthetic transformation. Herein, we report a method for intramolecular arene C?H etherification via an umpoled alcohol cyclization mediated by an I(III) N-HVI reagent. This approach provides access to functionalized chromane scaffolds from primary, secondary and tertiary alcohols via a cascade cyclization-iodonium salt formation, the latter providing a versatile functional handle for downstream derivatization. Computational studies support initial formation of an umpoled O-intermediate via I(III) ligand exchange, followed by competitive direct and spirocyclization/1,2-shift pathways. (Figure presented.).
Metal-Free Enantioselective Oxidative Arylation of Alkenes: Hypervalent-Iodine-Promoted Oxidative C?C Bond Formation
Shimogaki, Mio,Fujita, Morifumi,Sugimura, Takashi
, p. 15797 - 15801 (2016/12/16)
The enantioselective oxyarylation of (E)-6-aryl-1-silyloxylhex-3-ene was achieved using a lactate-based chiral hypervalent iodine(III) reagent in the presence of boron trifluoride diethyl etherate. The silyl ether promotes the oxidative cyclization, and enhances the enantioselectivity. In addition, the corresponding aminoarylation was achieved.
Synthesis of 2-tetralone derivatives by Bi(OTf)3-catalyzed intramolecular hydroarylation/isomerization of propargyl alcohols
Yun, Jihee,Park, Jungmin,Kim, Jaehyun,Lee, Kooyeon
, p. 1045 - 1048 (2015/02/19)
Compared to 1-tetralones, 2-tetralones are expensive, less stable, and difficult to synthesize. A concise Bi-catalyzed method was developed for the synthesis of 2-tetralones from 5-phenylpent-1-yn-3-ol derivatives. Diverse 2-tetralones were obtained in moderate to good yields under mild conditions.
Enantioselective halogenative semi-pinacol rearrangement: A stereodivergent reaction on a racemic mixture
Romanov-Michailidis, Fedor,Pupier, Marion,Gune, Laure,Alexakis, Alexandre
supporting information, p. 13461 - 13464 (2015/02/19)
An efficient, quantitative deracemization strategy for optically inactive allylic cycloalkanols has been achieved using the biphasic halogenative semi-pinacol reaction protocol. The resultant β-halo spiroketones, containing three contiguous stereogenic ce
Saturated heterocyclic carboxamide derivatives
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, (2008/06/13)
A saturated heterocyclic carboxamide derivative of the following general formula (I) and salts thereof which have platelet activating factor (PAF) antagonizing activity. STR1
MECHANISM OF INTRAMOLECULAR CYCLOALKYLATION OF 3-METHYL-3-PHENYL-1-BUTANOL IN THE PRESENCE OF D3PO4
Sakhabutdinov, A. G.,Usmanova, A. G.,Frolov, P. A.,Kushnarev, D. F.,Schmidt, F. K.
, p. 1452 - 1455 (2007/10/02)
The intramolecular cycloalkylation of isomeric 2-methyl-4-phenyl-2-butanol and 3-methyl-3-phenyl-1-butanol in D3PO4 is accompanied by hydrogen exchange with the formation of deuterated 1,1-dimethylindane.The distribution of the deuterium in the polymethylene ring shows that the reaction of the first alcohol takes place as a result of C5-cyclization of the χ-phenylalkyl cation, whereas the reaction of the second alcohol takes place by direct C5-cyclization and by cyclization of the χ-phenylalkyl cations formed as a result of 1,2- and 1,3-transfers of the phenyl group.
