68426-07-3Relevant articles and documents
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.).
Nickel-Catalyzed Cyanation of Unactivated Alkyl Chlorides or Bromides with Zn(CN)2
Xia, Aiyou,Xie, Xin,Chen, Haoyi,Zhao, Jidong,Zhang, Chunli,Liu, Yuanhong
supporting information, p. 7735 - 7739 (2019/01/03)
A nickel-catalyzed cyanation of unactivated secondary alkyl chlorides or bromides using less toxic Zn(CN)2 as the cyanide source has been developed. The reaction features the use of air-stable and inexpensive NiCl2·6H2O or Ni(acac)2 as the precatalysts and offers an efficient synthesis of a broad range of alkyl nitriles. Cyanation of primary alkyl chlorides or bromides was also achieved by reaction with Zn(CN)2 in the presence of n-Bu4NCl without the need of nickel catalyst.
Tandem Cross Coupling Reaction of Alcohols for Sustainable Synthesis of β-Alkylated Secondary Alcohols and Flavan Derivatives
Shee, Sujan,Paul, Bhaskar,Panja, Dibyajyoti,Roy, Bivas Chandra,Chakrabarti, Kaushik,Ganguli, Kasturi,Das, Ayan,Das, Gourab Kanti,Kundu, Sabuj
supporting information, p. 3888 - 3893 (2017/10/07)
A Ru(II) NHC complex (loading down to 0.001 mol%) catalyzed cross coupling of a broad range of aromatic, aliphatic and heterocyclic alcohols is reported. This protocol also functioned efficiently under solvent-free conditions. Remarkably, this catalytic system disclosed so far the highest TON of 288000 for the cross coupling of alcohols. Notably, this methodology was successfully applied for the one-pot synthesis of a range of flavan derivatives. A detailed DFT studies and kinetic experiments were performed to understand the reaction mechanism as well as the high reactivity of this catalytic system. (Figure presented.).
