52186-15-9Relevant academic research and scientific papers
Nickel-catalyzed guerbet type reaction: C-alkylation of secondary alcohols via double (de)hydrogenation
Babu, Reshma,Subaramanian, Murugan,Midya, Siba P.,Balaraman, Ekambaram
supporting information, p. 3320 - 3325 (2021/05/31)
Acceptorless double dehydrogenative cross-coupling of secondary and primary alcohols under nickel catalysis is reported. This Guerbet type reaction provides an atom- and a step-economical method for the C-alkylation of secondary alcohols under mild, benign conditions. A broad range of substrates including aromatic, cyclic, acyclic, and aliphatic alcohols was well tolerated. Interestingly, the C-alkylation of cholesterol derivatives and the double C-alkylation of cyclopentanol with various alcohols were also demonstrated.
Manganese-Catalyzed β-Alkylation of Secondary Alcohols with Primary Alcohols under Phosphine-Free Conditions
Liu, Tingting,Wang, Liandi,Wu, Kaikai,Yu, Zhengkun
, p. 7201 - 7207 (2018/07/21)
Manganese(I) complexes bearing a pyridyl-supported pyrazolyl-imidazolyl ligand efficiently catalyzed the direct β-alkylation of secondary alcohols with primary alcohols under phosphine-free conditions. The β-alkylated secondary alcohols were obtained in moderate to good yields with water formed as the byproduct through a borrowing hydrogen pathway. β-Alkylation of cholesterols was also effectively achieved. The present protocol provides a concise atom-economical method for C-C bond formation from primary and secondary alcohols.
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.).
Ruthenium(III)-Catalyzed β-Alkylation of Secondary Alcohols with Primary Alcohols
Wang, Qingfu,Wu, Kaikai,Yu, Zhengkun
, p. 1251 - 1256 (2016/06/01)
A Ru(III)-NNN complex bearing a pyridyl-supported pyrazolyl-imidazolyl ligand was synthesized and utilized as the catalyst for the direct β-alkylation of secondary alcohols with primary alcohols. β-Alkylated secondary alcohols were obtained in moderate to high yields with water formed as the byproduct through a hydrogen borrowing pathway. The present protocol provides a concise atom-economical and environmentally benign method for C-C bond formation.
Bifunctional Ru(II) complex catalysed carbon-carbon bond formation: an eco-friendly hydrogen borrowing strategy
Chakrabarti, Kaushik,Paul, Bhaskar,Maji, Milan,Roy, Bivas Chandra,Shee, Sujan,Kundu, Sabuj
, p. 10988 - 10997 (2016/12/06)
The atom economical borrowing hydrogen methodology enables the use of alcohols as alkylating agents for selective C-C bond formation. A bifunctional 2-(2-pyridyl-2-ol)-1,10-phenanthroline (phenpy-OH) based Ru(ii) complex (2) was found to be a highly efficient catalyst for the one-pot β-alkylation of secondary alcohols with primary alcohols and double alkylation of cyclopentanol with different primary alcohols. Exploiting the metal-ligand cooperativity in complex 2, several aromatic, aliphatic and heteroatom substituted alcohols were selectively cross-coupled in high yields using significantly low catalyst loading (0.1 mol%). An outer-sphere mechanism is proposed for this system as exogenous PPh3 has no significant effect on the rate of the reaction. Notably, this is a rare one-pot strategy for β-alkylation of secondary alcohols using a bifunctional Ru(ii)-complex. Moreover, this atom-economical methodology displayed the highest cumulative turn over frequency (TOF) among all the reported transition metal complexes in cross coupling of alcohols.
New cyclopentane derivatives as inhibitors of steroid metabolizing enzymes AKR1C1 and AKR1C3
Stefane, Bogdan,Brozic, Petra,Vehovc, Matej,Rizner, Tea Lanisnik,Gobec, Stanislav
experimental part, p. 2563 - 2571 (2009/10/17)
A series of cyclopentane derivatives was synthesized and evaluated for inhibition of the steroid metabolizing enzymes AKR1C1 and AKR1C3. Selective inhibitors that are active in the low micromolar range were identified. These compounds represent promising starting points in the development of new anticancer agents for the treatment of hormone-dependent forms of cancer and other diseases where AKR1C1 and AKR1C3 are involved.
