Organocatalytic γ′[C(sp3)-H] Functionalization of Ynones: An Unusual Approach for the Cyclopentannulation of Benzothiophenes

被引：9

作者：

Grover, Jagdeep ^{[1
]}

Raghu, Moluguri ^{[1
]}

Hazra, Raju ^{[1
]}

Mondal, Atanu ^{[1
]}

Ramasastry, S. S. V. ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res IISER Mohali, Organ Synth & Catalysis Lab, Dept Chem Sci, Sect 81, Manauli Po 140306, Punjab, India

来源：

SYNTHESIS-STUTTGART | 2018年 / 50卷 / 07期

关键词：

organophosphines; hydroalkylation; cyclopentannulation; ynones; benzothiophenes; H BOND ACTIVATION; HETEROCYCLIC ORTHO-QUINODIMETHANES; TOMITA ZIPPER CYCLIZATION; CATALYZED 4+2 ANNULATION; BAYLIS-HILLMAN REACTION; DIELS-ALDER REACTIONS; ONE-POT SYNTHESIS; C-H; STEREOSELECTIVE-SYNTHESIS; TRIENAMINE CATALYSIS;

D O I：

10.1055/s-0036-1591526

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient organocatalytic approach for the cyclopenta[b]annulation of benzothiophenes via gamma'[C(sp3)-H] functionalization of ynones is described. Nucleophilic addition of an organophosphine to the designed ynones generates heteroaryl-based ortho-quinodimethanes (oQDMs), which undergo carbocyclization to provide a variety of cyclopenta-fused benzothiophenes. This approach also constitutes an unusual organophosphine-catalyzed intramolecular hydroalkylation of ynones.

引用

页码：1462 / 1470

页数：9

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