Nickel-Catalyzed Reductive Cross-Coupling of Benzyl Halides with Aryl Halides

被引：11

作者：

Zhang, Qingchen ^{[1
,2
]}

Wang, Xuan ^{[1
,2
]}

Qian, Qun ^{[1
,2
]}

Gong, Hegui ^{[1
,2
,3
]}

机构：

[1] Shanghai Univ, Ctr Supramol Mat & Catalysis, 99 Shang Da Rd, Shanghai 200444, Peoples R China

[2] Shanghai Univ, Dept Chem, 99 Shang Da Rd, Shanghai 200444, Peoples R China

[3] Tongji Univ, Shanghai Key Lab Chem Assessment & Sustainabil, 1239 Siping Rd, Shanghai 200092, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2016年 / 48卷 / 17期

关键词：

nickel; cross-coupling; arylation; alkyl halide; catalysis; UNACTIVATED ALKYL-HALIDES; SINGLE-ELECTRON TRANSMETALATION; ALLYLIC CARBONATES; KETONE FORMATION; ORGANIC HALIDES; BROMIDES; ACIDS; DIARYLMETHANES; CARBOXYLATION; NUCLEOPHILES;

D O I：

10.1055/s-0035-1562442

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Systematic studies of the coupling of benzylic with aryl halides are presented. The optimized reaction conditions for electron-deficient aryl halides cannot be applied to the electron-rich or neutral counterparts, and vice versa. The excellent functional group tolerance and broad substrate scope may enable the current work to be useful for the construction of diaryl methane products.

引用

页码：2829 / 2836

页数：8

共 48 条

[1]

Ackerman LKG, 2015, CHEM SCI, V6, P1115, DOI [10.1039/c4sc03106g, 10.1039/C4SC03106G]

[2] Selective Cross-Coupling of Organic Halides with Allylic Acetates [J].

Anka-Lufford, Lukiana L. ;

Prinsell, Michael R. ;

Weix, Daniel J. .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22) :9989-10000

[3] Dialkyl Ether Formation by Nickel-Catalyzed Cross-Coupling of Acetals and Aryl Iodides [J].

Arendt, Kevin M. ;

Doyle, Abigail G. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (34) :9876-9880

[4] Iron Phosphine Catalyzed Cross-Coupling of Tetraorganoborates and Related Group 13 Nucleophiles with Alkyl Halides [J].

Bedford, Robin B. ;

Brenner, Peter B. ;

Carter, Emma ;

Clifton, Jamie ;

Cogswell, Paul M. ;

Gower, Nicholas J. ;

Haddow, Mairi F. ;

Harvey, Jeremy N. ;

Kehl, Jeffrey A. ;

Murphy, Damien M. ;

Neeve, Emily C. ;

Neidig, Michael L. ;

Nunn, Joshua ;

Snyder, Benjamin E. R. ;

Taylor, Joseph .

ORGANOMETALLICS, 2014, 33 (20) :5767-5780

[5] Nickel-Catalyzed Asymmetric Reductive Cross-Coupling Between Vinyl and Benzyl Electrophiles [J].

Cherney, Alan H. ;

Reisman, Sarah E. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (41) :14365-14368

[6] Catalytic Asymmetric Reductive Acyl Cross-Coupling: Synthesis of Enantioenriched Acyclic α,α-Disubstituted Ketones [J].

Cherney, Alan H. ;

Kadunce, Nathaniel T. ;

Reisman, Sarah E. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (20) :7442-7445

[7] Domino Iron Catalysis: Direct Aryl-Alkyl Cross-Coupling [J].

Czaplik, Waldemar Maximilian ;

Mayer, Matthias ;

Jacobi von Wangelin, Axel .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (03) :607-610

[8] Ni-Catalyzed Reductive Allylation of Unactivated Alkyl Halides with Allylic Carbonates [J].

Dai, Yijing ;

Wu, Fan ;

Zang, Zhenhua ;

You, Hengzhi ;

Gong, Hegui .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (03) :808-812

[9] Ni-catalyzed activation of α-chloroesters:: a simple method for the synthesis of α-arylesters and β-hydroxyesters [J].

Durandetti, Muriel ;

Gosmini, Corinne ;

Perichon, Jacques .

TETRAHEDRON, 2007, 63 (05) :1146-1153

[10] Cross-Electrophile Coupling: Principles of Reactivity and Selectivity [J].

Everson, Daniel A. ;

Weix, Daniel J. .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (11) :4793-4798

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