An efficient intermolecular [Pd]-catalyzed C–C and intramolecular [Cu]-catalyzed C–O bonds formation: synthesis of functionalized flavans and benzoxepine

Electrochemical Nozaki–Hiyama–Kishi Coupling: Scope, Applications, and Mechanism

“…In this work a variety of both coupling partners could be employed-encompassing a broad range of functional groups such as esters (8, 11, and 21), heterocycles (11, 16, and 17), ethers (10, 12, 20, and 23), alkynes (10), alkyl chlorides (9 and 19), sulphones (22), and imides (25). The range of suitable aldehydes was also expanded to include a,b-unsaturated (31) and aryl systems containing cyclopropanes (37), saturated heterocycles (33), and alkyl chlorides (32).…”

A concise route towards isoflavans

“…in dry DMF (120°C) for 24 hours]. [ 25 ] However, unfortunately, these conditions were not favorable in delivering the expected isoflavan 8a (entries 1, Table 3). At this stage, we reckoned that the use of excess base (KO t Bu) might have hampered the reaction.…”

“…Carrying forward our work on [TM]‐catalysis, [ 24 ] we have recently reported effective synthetic strategies for flavans. [ 25 ] In continuation of our interests, we have demonstrated a protocol affording neoflavans. [ 26 ] Herein; we disclose a new strategy delivering functionalized isoflavans.…”

Amine, Phenol, Alcohol, and Thiol Arylation

“…The intramolecular arylation of secondary and tertiary alcohols was also first reported in 1996 by Buchwald's group [63]. In 2012, Suchand et al reported an efficient three-step strategy for the synthesis of functionalized flavans, in which the intramolecular arylation of secondary arylbromo-alcohols was the key step [65]. Very interesting compounds were obtained from the corresponding bromoaryl and iodoaryl alcohols in very good yields.…”