Palladium-Catalyzed Ortho-Arylation of Carbamate-Protected Estrogens

被引：11

作者：

Bedford, Robin B. ^{[1
]}

Brenner, Peter B. ^{[1
]}

Durrant, Steven J. ^{[2
]}

Gallagher, Timothy ^{[1
]}

Mendez-Galvez, Carolina ^{[1
]}

Montgomery, Michelle ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Cantocks Close, Bristol BS8 1TS, Avon, England

[2] Vertex Pharmaceut Ltd Europe, 86-88 Jubilee Ave, Abingdon OX14 4RW, Oxon, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 09期

基金：

英国工程与自然科学研究理事会;

关键词：

BOND FORMATION; RECEPTOR;

D O I：

10.1021/acs.joc.6b00532

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalyzed ortho-arylation of diethyl carbamate-protected estrone and estriol with aryl iodides gives the 2-arylated analogues. Subsequent removal of the carbamate directing group furnishes 2-arylated estrone, estradiol, or estriol depending on the method used.

引用

页码：3473 / 3478

页数：7

共 22 条

[1] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[2] Modification of estrone at the 6, 16, and 17 positions:: Novel potent inhibitors of 17β-hydroxysteroid dehydrogenase type 1 [J].

Allan, GM ;

Lawrence, HR ;

Cornet, J ;

Bubert, C ;

Fischer, DS ;

Vicker, N ;

Smith, A ;

Tutill, HJ ;

Purohit, A ;

Day, JM ;

Mahon, MF ;

Reed, MJ ;

Potter, BVL .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (04) :1325-1345

[3] The neuroprotective actions of oestradiol and oestrogen receptors [J].

Arevalo, Maria-Angeles ;

Azcoitia, Inigo ;

Garcia-Segura, Luis M. .

NATURE REVIEWS NEUROSCIENCE, 2015, 16 (01) :17-29

[4] Breast Cancer, Estrogen Receptor and Ligands [J].

Bai, Zhenlin ;

Gust, Ronald .

ARCHIV DER PHARMAZIE, 2009, 342 (03) :133-149

[5] PENTAVALENT ORGANOBISMUTH REAGENTS .2. THE PHENYLATION OF PHENOLS [J].

BARTON, DHR ;

BHATNAGAR, NY ;

BLAZEJEWSKI, JC ;

CHARPIOT, B ;

FINET, JP ;

LESTER, DJ ;

MOTHERWELL, WB ;

PAPOULA, MTB ;

STANFORTH, SP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (12) :2657-2665

[6] Catalytic intermolecular ortho-arylation of phenols [J].

Bedford, RB ;

Limmert, ME .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (22) :8669-8682

[7] The catalytic intermolecular orthoarylation of phenols [J].

Bedford, RB ;

Coles, SJ ;

Hursthouse, MB ;

Limmert, ME .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (01) :112-114

[8] Simple rhodium-chlorophosphine pre-catalysts for the ortho-arylation of phenols [J].

Bedford, Robin B. ;

Betham, Michael ;

Caffyn, Andrew J. M. ;

Charmant, Jonathan P. H. ;

Lewis-Alleyne, Lesley C. ;

Long, Philip D. ;

Polo-Ceron, Dorian ;

Prashar, Sanjiv .

CHEMICAL COMMUNICATIONS, 2008, (08) :990-992

[9] Palladium-catalysed ortho-arylation of carbamate-protected phenols [J].

Bedford, Robin B. ;

Webster, Ruth L. ;

Mitchell, Charlotte J. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (23) :4853-4857

[10] Sex hormone effects on autonomic mechanisms of thermoregulation in humans [J].

Charkoudian, Nisha ;

Stachenfeld, Nina .

AUTONOMIC NEUROSCIENCE-BASIC & CLINICAL, 2016, 196 :75-80

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