Synthesis of tetrasubstituted olefins by Pd-catalyzed addition of arylboronic acids to internal alkynes

被引：51

作者：

Zhou, CX ^{[1
]}

Larock, RC ^{[1
]}

机构：

[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 02期

关键词：

D O I：

10.1021/ol047759q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tetrasubstituted olefins are readily prepared by the Pd-catalyzed cis addition of two aryl groups from an arylboronic acid to opposite ends of the triple bond of internal alkynes. The synthesis proceeds under very mild reaction conditions and tolerates a wide variety of functional groups, including alcohol, aldehyde, ester, TMS, and acetal groups.

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页码：259 / 262

页数：4

相关论文

共 37 条

[1] The first ligand-modulated oxidative Heck vinylation. Efficient catalysis with molecular oxygen as palladium(0) oxidant [J].

Andappan, MMS ;

Nilsson, P ;

Larhed, M .

CHEMICAL COMMUNICATIONS, 2004, (02) :218-219

[2] HIGH YIELDS OF UNSYMMETRICAL BIARYLS VIA CROSS-COUPLING OF ARYLBORONIC ACIDS WITH HALOARENES USING A MODIFIED SUZUKI-BELETSKAYA PROCEDURE [J].

CAMPI, EM ;

JACKSON, WR ;

MARCUCCIO, SM ;

NAESLUND, CGM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (20) :2395-2395

[3] PALLADIUM-CATALYZED CROSS-COUPLING OF ARYL AND ALKENYL BORONIC ACIDS WITH ALKENES VIA OXIDATIVE ADDITION OF A CARBON-BORON BOND TO PALLADIUM(0) [J].

CHO, CS ;

UEMURA, S .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 465 (1-2) :85-92

[4] Ordered mesoporous and microporous molecular sieves functionalized with transition metal complexes as catalysts for selective organic transformations [J].

De Vos, DE ;

Dams, M ;

Sels, BF ;

Jacobs, PA .

CHEMICAL REVIEWS, 2002, 102 (10) :3615-3640

[5] Mizoroki-heck type reaction of organoboron reagents with alkenes and alkynes.: A Pd(II)-catalyzed pathway with Cu(OAc)2 as an oxidant [J].

Du, XL ;

Suguro, M ;

Hirabayashi, K ;

Mori, A ;

Nishikata, T ;

Hagiwara, N ;

Kawata, K ;

Okeda, T ;

Wang, HF ;

Fugami, K ;

Kosugi, M .

ORGANIC LETTERS, 2001, 3 (21) :3313-3316

[6] Homocoupling of alkyl-, alkenyl-, and arylboronic acids [J].

Falck, JR ;

Mohapatra, S ;

Bondlela, M ;

Venkataraman, SK .

TETRAHEDRON LETTERS, 2002, 43 (45) :8149-8151

[7] Palladium catalysed tandem cyclisation-anion capture processes. Part 4: Organotin(IV) transfer agents [J].

Fretwell, P ;

Grigg, R ;

Sansano, JM ;

Sridharan, V ;

Sukirthalingam, S ;

Wilson, D ;

Redpath, J .

TETRAHEDRON, 2000, 56 (38) :7525-7539

[8]

GILLMANN T, 1994, SYNLETT, P649

[9] Palladium catalysed cascade cyclisation-anion capture, relay switches and molecular queues [J].

Grigg, R ;

Sridharan, V .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :65-87

[10] Heterocycles via Pd catalysed molecular queuing processes. Relay switches and the maximisation of molecular complexity [J].

Grigg, R ;

Sridharan, V .

PURE AND APPLIED CHEMISTRY, 1998, 70 (05) :1047-1057

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