Secondary Alkyl Groups in Palladium-Catalyzed Cross-Coupling Reactions

被引：16

作者：

Qureshi, Zafar ^{[1
]}

Toker, Christina ^{[1
]}

Lautens, Mark ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Davenport Res Labs, 80 St George St, Toronto, ON M5S 3H6, Canada

来源：

SYNTHESIS-STUTTGART | 2017年 / 49卷 / 01期

基金：

加拿大自然科学与工程研究理事会;

关键词：

palladium; homogenous catalysis; cross-coupling; secondary alkyl halides; C-H activation; C-H BONDS; TRANSITION-METAL-COMPLEXES; ASYMMETRIC-SYNTHESIS; ORGANOZINC REAGENTS; GRIGNARD-REAGENTS; OXIDATIVE ADDITION; C(SP(3))-H BONDS; ROOM-TEMPERATURE; ORGANIC HALIDES; ARYL BROMIDES;

D O I：

10.1055/s-0035-1561625

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Important classes of cross-coupling reactions are those leading to the incorporation of secondary alkyl groups. While early work in cross-coupling focused mainly on primary alkyl groups, the past decade has seen significant advances in introducing secondary and tertiary groups. This review will focus on the advances made in recent years referencing landmark publications where necessary. Expansion of scope, ease of reaction setup, and mechanistic considerations will be stressed. Applications of methodologies towards complex scaffolds and natural products will be also be evaluated.

引用

页码：1 / 16

页数：16

共 120 条

[1] The first palladium-catalyzed Sonogashira coupling of unactivated secondary alkyl bromides [J].

Altenhoff, G ;

Würtz, S ;

Glorius, F .

TETRAHEDRON LETTERS, 2006, 47 (17) :2925-2928

[2] Enantioselective synthesis of 2-methyl indolines by palladium catalysed asymmetric C(sp3)-H activation/cyclisation [J].

Anas, Saithalavi ;

Cordi, Alex ;

Kagan, Henri B. .

CHEMICAL COMMUNICATIONS, 2011, 47 (41) :11483-11485

[3] COMPLEX-INDUCED PROXIMITY EFFECTS - ENANTIOSELECTIVE SYNTHESES BASED ON ASYMMETRIC DEPROTONATIONS OF N-BOC-PYRROLIDINES [J].

BEAK, P ;

KERRICK, ST ;

WU, SD ;

CHU, JX .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) :3231-3239

[4] Regioselective, diastereoselective, and enantioselective lithiation-substitution sequences: Reaction pathways and synthetic applications [J].

Beak, P ;

Basu, A ;

Gallagher, DJ ;

Park, YS ;

Thayumanavan, S .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (11) :552-560

[5] C-GLYCOSIDES - PD/CU CO-CATALYZED THIOCARBOXYLATION OF STANNYL GLUCOPYRANOSIDES [J].

BELOSLUDTSEV, YY ;

BHATT, RK ;

FLACK, JR .

TETRAHEDRON LETTERS, 1995, 36 (33) :5881-5882

[6] PALLADIUM CATALYZED CROSS-COUPLING AND TANDEM CYCLIZATION-COUPLING OF ALPHA-HALO(THIO)ETHERS WITH ORGANOTINS [J].

BHATT, RK ;

SHIN, DS ;

FALCK, JR ;

MIOSKOWSKI, C .

TETRAHEDRON LETTERS, 1992, 33 (34) :4885-4888

[7] Palladium-Catalyzed Heck-Type Reactions of Alkyl Iodides [J].

Bloome, Kayla S. ;

McMahen, Rebecca L. ;

Alexanian, Erik J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (50) :20146-20148

[8] Negishi cross-coupling of secondary alkylzinc halides with aryl/heteroaryl halides using Pd-PEPPSI-IPent [J].

Calimsiz, Selcuk ;

Organ, Michael G. .

CHEMICAL COMMUNICATIONS, 2011, 47 (18) :5181-5183

[9] A complex catalytic cycle leading to a regioselective synthesis of o,o'-disubstituted vinylarenes [J].

Catellani, M ;

Frignani, F ;

Rangoni, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (1-2) :119-122

[10] A catalytic process based on sequential ortho-alkylation and vinylation of ortho-alkylaryl iodides via palladacycles [J].

Catellani, M ;

Cugini, F .

TETRAHEDRON, 1999, 55 (21) :6595-6602

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