TY - JOUR
T1 - Ruthenium-Catalyzed Reductive Coupling of Epoxides with Primary Alcohols via Hydrogen Transfer Catalysis
AU - Jana, Akash
AU - Chakraborty, Sayandip
AU - Sarkar, Koushik
AU - Maji, Biplab
N1 - Publisher Copyright:
© 2022 American Chemical Society.
PY - 2023/1/6
Y1 - 2023/1/6
N2 - Herein, we report the ruthenium-catalyzed synthesis of β-alkylated secondary alcohols via the regioselective ring-opening of epoxides with feedstock primary alcohols. The reaction utilized alcohol as the carbon source and the terminal reductant. Kinetic and labeling experiments elucidate the hydrogen transfer catalysis that operates via tandem Markovnikov selective transfer hydrogenation of terminal epoxides and hydrogen transfer-mediated cross-coupling of the resulting alcohol with primary alcohol substrates. A broad scope (40 examples including drugs/natural product derivatives) and excellent regioselectivity for a variety of substrates were shown.
AB - Herein, we report the ruthenium-catalyzed synthesis of β-alkylated secondary alcohols via the regioselective ring-opening of epoxides with feedstock primary alcohols. The reaction utilized alcohol as the carbon source and the terminal reductant. Kinetic and labeling experiments elucidate the hydrogen transfer catalysis that operates via tandem Markovnikov selective transfer hydrogenation of terminal epoxides and hydrogen transfer-mediated cross-coupling of the resulting alcohol with primary alcohol substrates. A broad scope (40 examples including drugs/natural product derivatives) and excellent regioselectivity for a variety of substrates were shown.
UR - http://www.scopus.com/inward/record.url?scp=85144775648&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.2c02354
DO - 10.1021/acs.joc.2c02354
M3 - Article
AN - SCOPUS:85144775648
SN - 0022-3263
VL - 88
SP - 310
EP - 318
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 1
ER -