Department of Chemistry and Pharmacy, Ludwig-Maximilians-University Munich, Butenandtstrasse 5-13, 81377 Munich, Germany.
Org Lett. 2015 Apr 17;17(8):1982-5. doi: 10.1021/acs.orglett.5b00738. Epub 2015 Mar 31.
The development of a sequential O-H/C-H bond functionalization of phenols initiated by the cationic gold(I)-catalyzed cyclization of 1-bromo-1,5-enynes to produce (2-bromocyclopent-2-en-1-yl)phenols is reported. This unprecedented domino transformation efficiently proceeds under mild conditions (5 mol % of (t-Bu)3PAuNTf2, CH2Cl2, 0-23 °C) via an intermediate aryl alkyl ether which collapses at ambient temperature to undergo a 1,2-hydride shift followed by C-H insertion of the phenol.
本文报道了一种通过 1-溴-1,5-炔的阳离子金（I）催化环化反应引发酚的顺序 O-H/C-H 键官能化的方法，生成（2-溴环戊-2-烯-1-基）苯酚。这种前所未有的串联转化在温和条件下（5 mol % 的 (t-Bu)3PAuNTf2、CH2Cl2、0-23°C）高效进行，通过一个中间芳基烷基醚进行，该醚在室温下分解，经历 1,2-氢化物转移，然后苯酚发生 C-H 插入。
