Synthesis of 2-Naphthols via Carbonylative Stille Coupling Reaction of 2-Bromobenzyl Bromides with Tributylallylstannane Followed by the Heck Reaction

被引：25
|
作者：
Dai, Yao [1 ]
Feng, Xiujuan [1 ]
Liu, Hesong [2 ]
Jiang, Hua [1 ]
Bao, Ming [1 ]
机构：
[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116024, Peoples R China
[2] Jilin Univ, Dept Dermatol & Venerol, Hosp 1, Changchun 130021, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 24期
基金：
中国国家自然科学基金;
关键词：
ADDITION-DIECKMANN CONDENSATION; CARBOCYCLE SYNTHESIS; BETA-NAPHTHOLS; ACID; FACILE; AGENT; DECOMPOSITION; REARRANGEMENT; CYCLIZATION; NAPHTHALENE;
D O I：
10.1021/jo201907t
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A method for the synthesis of 2-naphthols 4 is described. The carbonylative Stifle coupling reactions of 2-bromobenzyl bromides with tributylallylstannane to produce 2-bromobenzyl beta,gamma-unsaturated ketones 2 in satisfactory to excellent yields has been achieved. The isomerization of 2-bromobenzyl beta,gamma-unsaturated ketones 2 can readily occur under basic conditions to generate 2-bromobenzyl alpha,beta-unsaturated ketones 3. The 2-bromobenzyl alpha,beta-unsaturated ketones 3 can be transformed into 2-naphthols 4 via intramolecular Heck reaction in satisfactory to good yields.
引用
收藏
页码：10068 / 10077
页数：10
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