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

页码：10068 / 10077

页数：10

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