Palladium-catalyzed heteroallylation of unactivated alkenes - synthesis of citalopram

被引：45

作者：

Hewitt, Joanne F. M. ^{[1
]}

Williams, Lewis ^{[1
]}

Aggarwal, Pooja ^{[1
]}

Smith, Craig D. ^{[1
]}

France, David J. ^{[1
]}

机构：

[1] Univ Glasgow, Sch Chem, WestCHEM, Glasgow G12 8QQ, Lanark, Scotland

来源：

CHEMICAL SCIENCE | 2013年 / 4卷 / 09期

基金：

英国工程与自然科学研究理事会;

关键词：

PD(II)-CATALYZED COUPLING-CYCLIZATION; SOLUBLE RADICAL INITIATOR; N BOND FORMATION; CARBOAMINATION REACTIONS; EFFICIENT SYNTHESIS; C-N; 2-IODOALKANOIC ACID; FACILE SYNTHESIS; TETRAHYDROFURANS; DIAMINATION;

D O I：

10.1039/c3sc51222c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A palladium-catalyzed difunctionalization of unactivated alkenes with tethered nucleophiles is reported. The versatile reaction occurs with simple allylic halides and can be carried out under air. The methodology provides rapid access to a wide array of desirable heterocyclic targets, as illustrated by a concise synthesis of the widely prescribed antidepressant citalopram.

引用

页码：3538 / 3543

页数：6

共 101 条

[1] Metal-Catalyzed Cycloetherification Reactions of β,γ- and γ,δ-Allendiols: Chemo-, Regio-, and Stereocontrol in the Synthesis of Oxacycles [J].

Alcaide, Benito ;

Almendros, Pedro ;

Carrascosa, Rocio ;

Martinez del Campo, Teresa .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (44) :13243-13252

[2] Palladium-catalyzed ring-forming aminoacetoxylation of alkenes [J].

Alexanian, EJ ;

Lee, C ;

Sorensen, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (21) :7690-7691

[3] A new asymmetric Wacker-type cyclization and tandem cyclization promoted by Pd(II)-spiro bis(isoxazoline) catalyst [J].

Arai, MA ;

Kuraishi, M ;

Arai, T ;

Sasai, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (12) :2907-2908

[4] C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].

Beccalli, Egle M. ;

Broggini, Gianluigi ;

Martinelli, Michela ;

Sottocornola, Silvia .

CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365

[5]

Bogeso K. P., 1987, US Patent, Patent No. [4,650,884, 4650884, US 4650884]

[6]

BOGESO KP, 1979, Patent No. 4136193

[7] ORGANOPALLADIUM(IV) CHEMISTRY - OXIDATIVE ADDITION OF ORGANOHALIDES TO DIMETHYLPALLADIUM(II) COMPLEXES TO FORM ETHYL, SIGMA-BENZYL, AND SIGMA-ALLYLPALLADIUM(IV) COMPLEXES [J].

BYERS, PK ;

CANTY, AJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (10) :639-641

[8] SYNTHESIS OF TRANS-2,6-DIALKYLPIPERIDINES BY INTRAMOLECULAR AMIDOMERCURATION [J].

CARRUTHERS, W ;

WILLIAMS, MJ ;

COX, MT .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (18) :1235-1236

[9] TETRAHYDROPYRIDONES VIA INTRAMOLECULAR UREIDOMERCURATION [J].

DANISHEFSKY, S ;

TANIYAMA, E ;

WEBB, RR .

TETRAHEDRON LETTERS, 1983, 24 (01) :11-14

[10] Reactions of hypervalent iodine reagents with palladium: Mechanisms and applications in organic synthesis [J].

Deprez, Nicholas R. ;

Sanford, Melanie S. .

INORGANIC CHEMISTRY, 2007, 46 (06) :1924-1935

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