A new Suzuki-Heck-type coupling cascade: Indeno[1,2,3]-annelation of polycyclic aromatic hydrocarbons

被引：143

作者：

Wegner, HA

Scott, LT

de Meijere, A

机构：

[1] Univ Gottingen, Inst Organ Chem, D-37077 Gottingen, Germany

[2] Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 03期

关键词：

D O I：

10.1021/jo020367h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Under palladium catalysis, o-bromobenzeneboronic acid can be coupled with 1-bromonaphthalene (6) and with oligocyclic bromoarenes to furnish indeno-annelated polycyclic aromatic hydrocarbons 1-4 and 25 in a single operation in moderate to good yields (27-87%). Alternatively, o-dibromoarenes and 1,2-dibromocycloalkenes can be cross-coupled with 1-naphthaleneboronic acid under the same conditions to yield analogous products (6-87%), and indenocorannulene (19) can be prepared likewise in a single step from pinacol corannuleneboronate (18) (40%).

引用

页码：883 / 887

页数：5

共 24 条

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