Copper(II)-catalyzed Chan-Lam cross-coupling: chemoselective N-arylation of aminophenols

被引：53

作者：

Reddy, A. Siva ^{[1
,2
]}

Reddy, K. Ranjith ^{[1
,2
]}

Rao, D. Nageswar ^{[1
,2
]}

Jaladanki, Chaitanya K. ^{[3
]}

Bharatam, Prasad V. ^{[3
]}

Lam, Patrick Y. S. ^{[4
]}

Das, Parthasarathi ^{[1
,2
]}

机构：

[1] Indian Inst Integrat Med, CSIR, Med Chem Div, Jammu 180001, India

[2] Acad Sci & Innovat Res AcSIR, New Delhi 110025, India

[3] Natl Inst Educ & Res NIPER, Dept Med Chem, Mohali 160062, Punjab, India

[4] Baruch S Blumberg Inst, 3805 Old Easton Rd, Doylestown, PA 18902 USA

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 04期

关键词：

C-H AMINATION; BOND FORMATION SYNTHESIS; ARYL BORONIC ACIDS; ONE-POT SYNTHESIS; ARYLBORONIC ACIDS; O-ARYLATION; CATALYZED ARYLATION; PHENYLBORONIC ACIDS; CONVENIENT ROUTE; COPPER;

D O I：

10.1039/c6ob02444k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Copper(II)-catalyzed boronic acid promoted chemoselective N-arylation of unprotected aminophenols has been developed. Selective N-arylation of 3-aminophenol is achieved with a Cu(OAc)(2)/AgOAc combination in MeOH at rt, whereas the chemoselective N-arylated products of 4-aminophenol can be obtained with a Cu(OAc)(2)/Cs2CO3 system and benzoic acid as an additive. These ligand-free conditions and "open-flask" chemistry are robust and compatible with a wide range of functional groups. The mechanistic investigation for this selective N-arylation has been studied by considering Density Functional Theory (DFT) calculations.

引用

页码：801 / 806

页数：6

共 76 条

[1] Targeted cancer therapies [J].

Aggarwal, Saurabh .

NATURE REVIEWS DRUG DISCOVERY, 2010, 9 (06) :427-428

[2] Copper-catalyzed coupling of arylboronic acids and amines [J].

Antilla, JC ;

Buchwald, SL .

ORGANIC LETTERS, 2001, 3 (13) :2077-2079

[3] C-N bond forming cross-coupling reactions: an overview [J].

Bariwal, Jitender ;

Van der Eycken, Erik .

CHEMICAL SOCIETY REVIEWS, 2013, 42 (24) :9283-9303

[4] The Complementary Competitors: Palladium and Copper in C-N Cross-Coupling Reactions [J].

Beletskaya, Irina P. ;

Cheprakov, Andrei V. .

ORGANOMETALLICS, 2012, 31 (22) :7753-7808

[5]

Benjamin H., 2011, CHEM SCI, V2, P312

[6]

Berlinck R., 2007, Modern Alkaloids: Structure, Isolation, Synthesis and Biology, P305

[7] Kinase Domain Mutations in Cancer: Implications for Small Molecule Drug Design Strategies [J].

Bikker, Jack A. ;

Brooijmans, Natasja ;

Wissner, Allan ;

Mansour, Tarek S. .

JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (06) :1493-1509

[8] New N- and O-arylations with phenylboronic acids and cupric acetate [J].

Chan, DMT ;

Monaco, KL ;

Wang, RP ;

Winters, MP .

TETRAHEDRON LETTERS, 1998, 39 (19) :2933-2936

[9]

Chan DMT, 2005, BORONIC ACIDS: PREPARATION AND APPLICATIONS IN ORGANIC SYNTHESIS AND MEDICINE, P205, DOI 10.1002/3527606548.ch5

[10] An efficient diamine copper complex-catalyzed coupling of arylboronic acids with imidazoles [J].

Collman, JP ;

Zhong, M .

ORGANIC LETTERS, 2000, 2 (09) :1233-1236

← 1 2 3 4 5 6 7 8 →