A ZnI2-catalyzed regioselective cascade 1,4-conjugate addition/5-exo-dig annulation pathway for one-pot access to heterobiaryl frameworks

被引：23

作者：

He, Xinwei ^{[1
,2
,3
]}

Choy, Pui Ying ^{[1
,2
]}

Leung, Man Pan ^{[1
,2
]}

Yuen, On Ying ^{[1
,2
]}

Liu, Tianyi ^{[1
,2
]}

Shang, Yongjia ^{[3
]}

Kwong, Fuk Yee ^{[1
,2
]}

机构：

[1] Chinese Univ Hong Kong, State Key Lab Synthet Chem, Shatin, Hong Kong, Peoples R China

[2] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong, Peoples R China

[3] Anhui Normal Univ, Coll Chem & Mat Sci, Key Lab Funct Mol Solids, Minist Educ, Wuhu 241000, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2019年 / 55卷 / 100期

关键词：

ORTHO-QUINONE METHIDES; BAYLIS-HILLMAN ACETATES; PROPARGYLIC ALCOHOLS; EFFICIENT SYNTHESIS; NATURAL-PRODUCT; DERIVATIVES; BENZOFURAN; FURANS; CONSTRUCTION; HETEROCYCLES;

D O I：

10.1039/c9cc07054k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Facile access to pi-extended heterobiaryl compounds via a non-cross-coupling strategy has been achieved. In the presence of an inexpensive ZnI2 catalyst and versatile propargylamine and beta-naphthol (or beta-naphthylamine and beta-naphthyl mercaptan) starting materials, a variety of sterically hindered heterobiaryl frameworks can be easily obtained. The present catalytic system offers excellent selectivity, good-to-excellent product yields, and good functional group tolerance including, for instance, -CN, -COOH, -C(O)R, -Br and -Cl groups. This cyclization process is proposed to proceed via in situ generated alkynyl o-quinone methides (o-AQMs), following a cascade intermolecular 1,4-conjugate addition/5-exo-dig annulation/1,3-H shift pathway.

引用

页码：15069 / 15072

页数：4

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