Potassium hydrogen sulfate adsorbed on chromatography-grade silica gel activates electron-rich aromaticterminalolefins towards nucleophilic attack at the benzylic position by alcohols. Temperature plays a crucial role and facilitates suppressing nucleophilic reaction in favor of dimerization of the terminalolefin.
Reactivity-selectivity in the Swern oxidation of alcohols using dimethyl sulfoxide-oxalyl chloride
作者:Michael Marx、Thomas T. Tidwell
DOI:10.1021/jo00179a009
日期:1984.3
NBS-Catalyzed Hydroamination and Hydroalkoxylation of Activated Styrenes
作者:Siva Kumar Talluri、Arumugam Sudalai
DOI:10.1021/ol047402m
日期:2005.3.1
N-Bromosuccinimide efficiently catalyzes the hydroamination and hydroalkoxylation of activated styrenes using tosylamides, carbamates, and alcohols as the nucleophiles to afford amino and ether derivatives, respectively. Both the processes give good to excellent yields of the products with 100% regioselectivity (Markovnikov fashion).
Selective Catalytic Synthesis of Unsymmetrical Ethers from the Dehydrative Etherification of Two Different Alcohols
作者:Junghwa Kim、Dong-Hwan Lee、Nishantha Kalutharage、Chae S. Yi
DOI:10.1021/cs5012537
日期:2014.11.7
The cationic ruthenium–hydride complex [(C6H6)(PCy3)(CO)RuH]+BF4– catalyzes selective etherification of two different alcohols to form unsymmetrically substituted ethers. The catalytic method exhibits a broad substrate scope while tolerating a range of heteroatom functional groups in forming unsymmetrical ethers, and it is successfully used to directly synthesize a number of highly functionalized chiral
阳离子钌-氢化物配合物[(C 6 H ^ 6)(PCY 3)(CO)期RuH] + BF 4 -催化两个不同的醇的醚化的选择性,以形成不对称取代的醚。该催化方法在形成不对称醚时可容忍一定范围的杂原子官能团,因此具有广阔的底物范围,并且已成功用于直接合成许多高度官能化的手性非外消旋醚。