trans-Chloro(1-Naphthyl)bis(triphenylphosphine)nickel(II)/PCy3 Catalyzed Cross-Coupling of Aryl and Heteroaryl Neopentylglycolboronates with Aryl and Heteroaryl Mesylates and Sulfamates at Room Temperature

被引：70

作者：

Leowanawat, Pawaret ^{[1
]}

Zhang, Na ^{[1
]}

Safi, Mehtap ^{[1
]}

Hoffman, David J. ^{[1
]}

Fryberger, Miriam C. ^{[1
]}

George, Aiswaria ^{[1
]}

Percec, Virgil ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 06期

基金：

美国国家科学基金会;

关键词：

C-O ACTIVATION; NI(II)-(SIGMA-ARYL) COMPLEX; EFFICIENT CATALYST; HALIDES; LIGAND; ARENESULFONATES; CHLORIDES; BORYLATION; TOSYLATES; CYANATION;

D O I：

10.1021/jo3001194

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

trans-Chloro(1-naphthyl)bis(triphenylphosphine)nickel-(II) complex/PCy3 system has been successfully applied as catalyst for the Suzuki-Miyaura cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates in THF at room temperature. This cross-coupling reaction tolerates various functional groups, including keto, imino, ester, ether, and cyano. Together with the nickel-catalyzed, one-pot, two-step neopentylglycolborylation, this bench stable and inexpensive Ni(II)-based catalyst can be utilized as an alternative to Ni(COD)(2)/PCy3 to provide an inexpensive, robust, and convenient synthesis of biaryl and heterobiaryl compounds.

引用

页码：2885 / 2892

页数：8

共 57 条

[1] N,N-Diethyl O-Carbamate: Directed Metalation Group and Orthogonal Suzuki-Miyaura Cross-Coupling Partner [J].

Antoft-Finch, Aurora ;

Blackburn, Tom ;

Snieckus, Victor .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (49) :17750-17752

[2] Rapid Nickel-Catalyzed Suzuki-Miyaura Cross-Couplings of Aryl Carbamates and Sulfamates Utilizing Microwave Heating [J].

Baghbanzadeh, Mostafa ;

Pilger, Christian ;

Kappe, C. Oliver .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (05) :1507-1510

[3]

Brandsma L., 1998, SPRINGER LAB, P15

[4] NEW NICKEL-CATALYZED SYNTHESIS OF AROMATIC NITRILES [J].

CASSAR, L .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1973, 54 (JUN16) :C57-C58

[5]

CASSAR L, 1974, ADV CHEM SER, P252

[6] ALKYLS AND ARYLS OF TRANSITION METALS .3. NICKEL(II) DERIVATIVES [J].

CHATT, J ;

SHAW, BL .

JOURNAL OF THE CHEMICAL SOCIETY, 1960, (APR) :1718-1729

[7] Ni(II)-(σ-Aryl) complex:: A facile, efficient catalyst for nickel-catalyzed carbon-nitrogen coupling reactions [J].

Chen, Chen ;

Yang, Lian-Ming .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (16) :6324-6327

[8] Nickel(II)-aryl complexes as catalysts for the Suzuki cross-coupling reaction of chloroarenes and arylboronic acids [J].

Chen, Chen ;

Yang, Lian-Ming .

TETRAHEDRON LETTERS, 2007, 48 (13) :2427-2430

[9] Nickel-Catalyzed Cross-Coupling of Aryl Phosphates with Arylboronic Acids [J].

Chen, Hu ;

Huang, Zhongbin ;

Hu, Xiaoming ;

Tang, Guo ;

Xu, Pengxiang ;

Zhao, Yufen ;

Cheng, Chien-Hong .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (07) :2338-2344

[10] Potassium organotrifluoroborates: New perspectives in organic synthesis [J].

Darses, Sylvain ;

Genet, Jean-Pierre .

CHEMICAL REVIEWS, 2008, 108 (01) :288-325

← 1 2 3 4 5 6 →