Department of Chemistry, National Taiwan Normal University, 88 Ding-Jou Road, Section 4, Taipei 11677, Taiwan, Republic of China.
J Org Chem. 2011 May 20;76(10):4027-33. doi: 10.1021/jo200445p. Epub 2011 Apr 29.
The gold(I)-catalyzed hydroarylation of cyclohexa-1,3-dienes bearing an aryl group and a gem-diester in the tether proceeds in a 1,4-addition manner and in a diastereoselective fashion to afford perhydrophenanthrene rings. The reaction proceeded via attack of the aryl group onto the gold-activated cyclic dienes followed by rearomatization and protodeauration to generate perhydrophenanthrenes in good yields. This hydroarylation can be applied to the synthesis of perhydrocyclohepta[a]naphthalenes from aryl-tethered cycloheptadienes and the gold(I) catalyst.
金（I）催化的带有芳基和偕二酯的环己-1,3-二烯的氢芳基化反应以 1,4-加成方式进行，并具有立体选择性，生成全氢菲环。该反应通过芳基进攻金活化的环状二烯进行，然后进行再芳构化和脱金反应，以高产率生成全氢菲。这种氢芳基化可以应用于芳基桥连的环庚二烯到全氢环庚[a]萘的合成，以及金（I）催化剂的应用。
