光化学反应条件助力Williamson烯丙基合成法无法实现的大位阻烯丙基的制备！

latiles were removed under reduced pressure, purification by flash column chromatography on silica gel (100:0–98:2, hexane/Et2O) gave the 3aa (32.3 mg, 0.15 mmol, 74% isolated yield) as a pale yellow oil.

The reaction in Table 1, entry 13 is representative (limiting reagent: alcohol).

In a glovebox, to an oven-dried vial with a stirring bar was added photoredox catalyst PTH-1 (3.7 mg, 0.01 mmol), Co-1 (1.2 mg, 0.002 mmol), HX-1 (5.4 mg, 0.02 mmol) and DCM (500 μL). Then, cyclopentanol 1a (18.1 µL, 0.2 mmol) and 4-phenyl-1-butene 2a (60.1 µL, 0.4 mmol) were added to the reaction mixture. After sealing the vial with a cap and removal from the glove box, the reaction was stirred and irradiated with a 34W blue LED (0.5 cm away) with a cooling fan to keep the temperature around 40 o C (Figure S2). After 24 h, the reaction was quenched with a short plug of silica gel using diethyl ether. After volatiles were removed under reduced pressure, purification by flash column chromatography on silica gel (100:0–98:2, hexane/Et2O) gave the 3aa (37.6 mg, 0.17 mmol, 86% isolated yield.) as a pale yellow oil.

简要

一、 StrategicApplications of Named Reactions in Organic Synthesis, László Kürti and BarbaraCzakó, Williamson ether synthesis., page 484-485.

二、A Triple Photoredox/Cobalt/Brønsted Acid Catalysis Enabling Markovnikov Hydroalkoxylation of Unactivated Alkenes； Masanari Nakagawa,∥ Yuki Matsuki,∥ Kazunori Nagao,* and Hirohisa Ohmiya*； J. Am. Chem. Soc. 2022, 144, 7953−7959。

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