Synthesis of 7,7′-Dihydroxy-8,8′-biquinolyl (azaBINOL) via Pd-Catalyzed Directed Double C-H Functionalization of 8,8′-Biquinolyl: Emergence of an Atropos from a Tropos State

被引：24

作者：

Wang, Chao ^{[1
]}

Flanigan, Darrin M. ^{[1
]}

Zakharov, Lev N. ^{[1
]}

Blakemore, Paul R. ^{[1
]}

机构：

[1] Oregon State Univ, Dept Chem, Corvallis, OR 97331 USA

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 15期

基金：

美国国家科学基金会;

关键词：

REDUCTIVE ELIMINATION; ASYMMETRIC CATALYSIS; DIRECT ARYLATION; PALLADIUM; BONDS; RESOLUTION; OXIDATION; ARENES; HALOGENATION; ACTIVATION;

D O I：

10.1021/ol201539d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

7,7'-Dihydroxy-8,8'-biquinolyl(azaBINOL) was prepared from 2-chloroaniline in four steps: (1) the Skraup reaction, (2) Ni-catalyzed reductive coupling of 8-chloroquinoline, (3) Pd(II)-catalyzed double C-H functionalization of 8,8'-biquinolyl mediated by Phl(OAc)(2), and (4) saponification. During the third step, an axially chiral (atropos type) biaryl molecule was directly generated from an essentially achiral (tropos type) biaryl starting material.

引用

页码：4024 / 4027

页数：4

共 15 条

[1] Axially Chiral Bifunctional 8,8′-Biquinolyl: Synthesis of 7,7′-Dihydroxymethyl-8,8′-biquinolyl via Pd-Catalyzed Double C-H Oxidation of 7,7′-Dimethyl-8,8′-biquinolyl
Kitamura, Mitsuru
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JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (09): : 3956 - 3960
[2] Enzymatic resolution of 7,7′-dihydroxy-8,8′-biquinolyl dipentanoate and its conversion to 2,2′-di-tert-butyl-7,7′-dihydroxy-8,8′-biquinolyl
Blakemore, Paul R.
Milicevic, Selena D.
Zakharov, Lev N.
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (24): : 9368 - 9371
[3] Resolution, enantiomerization kinetics, and chiroptical properties of 7,7′-dihydroxy-8,8′-biquinolyl
Blakemore, Paul R.
Kilner, Colin
Milicevic, Selena D.
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (21): : 8212 - 8218
[4] 7,7′-dihydroxy-8,8′-biquinolyl:: Investigation of a new atropisomeric chiral entity.
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Milicevic, SD
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U346 - U346
[5] Silylcyanation of Aldehydes, Ketones, and Imines Catalyzed by a 6,6′-Bis-sulfonamide Derivative of 7,7′-Dihydroxy-8,8′-biquinolyl (azaBINOL)
Sephton, Selena Milicevic
Wang, Chao
Zakharov, Lev N.
Blakemore, Paul R.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (17) : 3249 - 3260
[6] 7-Hydroxy-8-(2-hydroxynaphthalen-1-yl)quinoline: A new member of the azaBINOL family with superior configurational stability and solubility to 7,7′-dihydroxy-8,8′-biquinolyl
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ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
[7] Determination of pKa values for diether derivatives of 7,7′-dihydroxy-8,8′-biquinolyl:: Dependence of basicity on interannular dihedral angle
Blakemore, Paul R.
Milicevic, Selena D.
Perera, Hasini
Shvarev, Alexey
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SYNTHESIS-STUTTGART, 2008, (14): : 2271 - 2277
[8] ORGN 765-Lone-pair/lone-pair proximity effects in a series of cyclic diethers derived from 7,7'-dihydroxy-8,8'-biquinolyl
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Milicevic, Selena D.
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ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234
[9] ORGN 999-Evaluation of 6,6'-bis(methylaminosulfonyl)-7,7'-dihydroxy-8,8'-biquinolyl in reaction catalysis with and without metal additives
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Milicevic, Selena D.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234
[10] Harnessing anionic rearrangements on the benzenoid ring of quinoline for the synthesis of 6,6′-disubstituted 7,7′-dihydroxy-8,8′-biquinolyls
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JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01): : 373 - 376

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