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

页码：3142 / 3145

页数：4

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