C-F Activation for C(sp2)-C(sp3) Cross-Coupling by a Secondary Phosphine Oxide (SPO)-Nickel Complex

被引：21

作者：

Mueller, Valentin ^{[1
]}

Ghorai, Debasish ^{[1
]}

Capdevila, Lorena ^{[2
,3
]}

Messinis, Antonis M. ^{[1
]}

Ribas, Xavi ^{[2
,3
]}

Ackermann, Lutz ^{[1
,4
]}

机构：

[1] Georg August Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany

[2] Univ Girona, Inst Quim Computac & Catalisi IQCC, E-17003 Girona, Catalonia, Spain

[3] Univ Girona, Dept Quim, E-17003 Girona, Catalonia, Spain

[4] Georg August Univ Gottingen, Wohler Res Inst Sustainable Chem WISCh, D-37077 Gottingen, Germany

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 17期

基金：

欧洲研究理事会;

关键词：

ALKYL GRIGNARD-REAGENTS; BOND ACTIVATION; ARYL BROMIDES; REDUCTIVE ELIMINATION; GROUP ISOMERIZATION; H ACTIVATION; HALIDES; TERTIARY; PRELIGANDS; CATALYSIS;

D O I：

10.1021/acs.orglett.0c02609

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A secondary phosphine oxide (SPO)-nickel catalyst allowed the activation of otherwise inert C-F bonds of unactivated arenes in terms of challenging couplings with primary and secondary alkyl Grignard reagents. The C-F activation is characterized by mild reaction conditions and high levels of branched selectivity. Electron-rich and electron-deficient arenes were suitable electrophiles for this transformation. In addition, this strategy also proved suitable to heterocycles and for the activation of C-O bonds under slightly modified conditions.

引用

页码：7034 / 7040

页数：7

共 113 条

[1] Catalytic arylation reactions by C-H bond activation with aryl tosylates [J].

Ackermann, L ;

Althammer, A ;

Born, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (16) :2619-2622

[2] Efficient aryl-(hetero)aryl coupling by activation of C-Cl and C-F bonds using nickel complexes of air-stable phosphine oxides [J].

Ackermann, L ;

Born, R ;

Spatz, JH ;

Meyer, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (44) :7216-7219

[3]

Ackermann L, 2009, MODERN ARYLATION METHODS, P1

[4] Phosphine oxides as preligands in ruthenium-catalyzed arylations via C-H bond functionalization using aryl chlorides [J].

Ackermann, L .

ORGANIC LETTERS, 2005, 7 (14) :3123-3125

[5]

Ackermann L., 2012, HDB GREEN CHEM, V7, P259

[6] Air- and moisture-stable secondary phosphine oxides as preligands in catalysis [J].

Ackermann, Lutz .

SYNTHESIS-STUTTGART, 2006, 10 (10) :1557-1571

[7] User-Friendly [(Diglyme)NiBr2]-Catalyzed Direct Alkylations of Heteroarenes with Unactivated Alkyl Halides through C-H Bond Cleavages [J].

Ackermann, Lutz ;

Punji, Benudhar ;

Song, Weifeng .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (18) :3325-3329

[8] Air-Stable Diaminophosphine Sulfides as Preligands for Nickel-Catalyzed Cross-Couplings of Unactivated Fluoro(hetero)arenes [J].

Ackermann, Lutz ;

Wechsler, Cindy ;

Kapdi, Anant R. ;

Althammer, Andreas .

SYNLETT, 2010, (02) :294-298

[9] Modern magnesium organic chemie [J].

Ackermann, Lutz ;

Althammer, Andreas .

CHEMIE IN UNSERER ZEIT, 2009, 43 (02) :74-83

[10] Mechanistic Study of β-Hydrogen Elimination from Organoplatinum(II) Enolate Complexes [J].

Alexanian, Erik J. ;

Hartwig, John F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (46) :15627-15635

← 1 2 3 4 5 6 7 8 9 10 →