Synthesis of Substituted Benzenes via Bi(OTf)3-Mediated Intramolecular Carbonyl Allylation of a-Prenyl or α-Geranyl β-Arylketosulfones

被引：53
作者：
Chang, Meng-Yang [1 ]
Cheng, Yu-Chieh [1 ]
Lu, Yi-Ju [1 ]
机构：
[1] Kaohsiung Med Univ, Dept Med & Appl Chem, Kaohsiung 80708, Taiwan
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 12期
关键词：
ORGANIC-CHEMISTRY APPLICATION; CROSS-COUPLING REACTIONS; BISMUTH(III) TRIFLATE; REGIOSELECTIVE SYNTHESIS; 2+2+2 CYCLOADDITION; CATALYZED SYNTHESIS; ALLYLIC ALKYLATION; TERTIARY ALCOHOLS; KETO SULFONES; CYCLIZATION;
D O I：
10.1021/acs.orglett.5b01461
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Intramolecular carbonyl allylation of alpha-prenyl or alpha-geranyl beta-arylketosulfones 5 in the presence of molecule sieves (MS) affords substituted benzenes 6-7 in moderate to good yields. The facile transformation proceeds by a synthetic sequence starting with the alpha-prenylation or alpha-geranylation of 1 and the Bi(OTf)(3)-mediated annulation of 5 followed by a sequential desulfonative aromatization or then an intramolecular FriedelCrafts alkylation. A plausible mechanism has been studied and proposed.
引用
收藏
页码：3142 / 3145
页数：4
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