Rhodium-Catalyzed Direct C-H Phosphorylation of (Hetero)arenes Suitable for Late-Stage Functionalization

被引：51

作者：

Min, Minsik ^{[1
,2
]}

Kang, Dahye ^{[1
,2
]}

Jung, Sungwoo ^{[1
,2
]}

Hong, Sungwoo ^{[1
,2
]}

机构：

[1] Korea Adv Inst Sci & Technol, Dept Chem, Taejon 305701, South Korea

[2] Inst for Basic Sci Korea, Ctr Catalyt Hydrocarbon Functionalizat, Taejon 305701, South Korea

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 08期

关键词：

catalyst; C-H activation; late-stage modification; phosphorylation; rhodium; CARBON-CARBON BONDS; PHOSPHINE OXIDES; ACTIVATION; ARYL; ALKYNYLATION; LIGANDS; ALKYNES; ARENES; ACIDS; IDENTIFICATION;

D O I：

10.1002/adsc.201600014

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Efficient rhodium-catalyzed direct C-H phosphorylation of (hetero)arenes was developed. Various directing groups and a wide range of substrates, including heterocycles, can be utilized in this C-H phosphorylation process, allowing for the rapid installation of the phosphonate group into medicinally and biologically important privileged scaffolds. The efficient and straightforward method could serve as a new tool to streamline late-stage C-H functionalization for preparing aryl phosphonates, which are important structural motif in synthetic and medicinal chemistry.

引用

页码：1296 / 1301

页数：6

共 73 条

[1] Air-stable phosphine oxides as preligands for catalytic activation reactions of C-Cl, C-F, and C-H bonds [J].

Ackermann, L ;

Born, R ;

Spatz, JH ;

Althammer, A ;

Gschrei, CJ .

PURE AND APPLIED CHEMISTRY, 2006, 78 (02) :209-214

[2] Phenylphosphonic acid functionalized poly [aryloxyphosphazenes] [J].

Allcock, HR ;

Hofmann, MA ;

Ambler, CM ;

Morford, RV .

MACROMOLECULES, 2002, 35 (09) :3484-3489

[3]

[Anonymous], 2012, ANGEW CHEM, DOI DOI 10.1002/ANIE.201201666

[4]

[Anonymous], 2013, ANGEW CHEM, V125, P9983

[5] Phosphorus Lewis acids: emerging reactivity and applications in catalysis [J].

Bayne, J. M. ;

Stephan, D. W. .

CHEMICAL SOCIETY REVIEWS, 2016, 45 (04) :765-774

[6] INTERCONVERSION REACTIONS BETWEEN SUBSTITUTED PHOSPHINOUS ACID-PHOSPHINITO COMPLEXES OF PLATINUM(II) AND THEIR CAPPING REACTIONS WITH BORON TRIFLUORIDE-DIETHYL ETHERATE [J].

BEAULIEU, WB ;

RAUCHFUSS, TB ;

ROUNDHILL, DM .

INORGANIC CHEMISTRY, 1975, 14 (07) :1732-1734

[7] Revisiting the Hirao cross-coupling: improved synthesis of aryl and heteroaryl phosphonates [J].

Belabassi, Yamina ;

Alzghari, Saeed ;

Montchamp, Jean-Luc .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2008, 693 (19) :3171-3178

[8] Phosphorus-Carbon Bond Formation: Palladium-Catalyzed Cross-Coupling of H-Phosphinates and Other P(O)H-Containing Compounds [J].

Berger, Olivier ;

Petit, Christelle ;

Deal, Eric L. ;

Montchamp, Jean-Luc .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (07) :1361-1373

[9] Mechanistic Study of the Oxidative Coupling of Styrene with 2-Phenylpyridine Derivatives Catalyzed by Cationic Rhodium(III) via C-H Activation [J].

Brasse, Mikael ;

Campora, Juan ;

Ellman, Jonathan A. ;

Bergman, Robert G. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (17) :6427-6430

[10] Rh(III)-Catalyzed Oxidative Coupling of N-Aryl-2-aminopyridine with Alkynes and Alkenes [J].

Chen, Jinlei ;

Song, Guoyong ;

Pan, Cheng-Ling ;

Li, Xingwei .

ORGANIC LETTERS, 2010, 12 (23) :5426-5429

← 1 2 3 4 5 6 7 8 →