Pd(0)-catalysed formation of diarylated dienes from propargyl carbonates and organoboron and organotin(IV) reagents

被引：27

作者：

Böhmer, J ^{[1
]}

Grigg, R ^{[1
]}

机构：

[1] Univ Leeds, Sch Chem, Mol Innovat Divers & Automated Synth Ctr, Leeds LS2 9JT, W Yorkshire, England

来源：

TETRAHEDRON | 1999年 / 55卷 / 47期

关键词：

catalysis; allenylpalladium(II); pi-allylpalladium(II); boronic acids; Stille coupling; Suzuki coupling;

D O I：

10.1016/S0040-4020(99)00831-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 1,1-dimethylbutyne-1,4-diol derivative 1 reacts with 2 mol. equiv. of organoboron (NaBPh4 arylboronic acids) and organotin(IV) reagents to give 1,1-dimethyl-2,3-disubstituted butadienes in good yield via allenylpalladium(II) and vinylidene-pi-allylpalladium(II) intermediates. Unsubstituted esters 6 and butyne dicarbonate 7 lead to symmetrical dienes 8. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：13463 / 13470

页数：8

相关论文

共 13 条

[1] DISULFUR MONOXIDE - REACTION WITH DIENES [J].

DODSON, RM ;

SRINIVASAN, V ;

SAUERS, RF ;

SHARMA, KS .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (15) :2367-+

[2] Palladium catalysed triscyclisation-anion capture queuing cascades. [J].

Grigg, R ;

Rasul, R ;

Savic, V .

TETRAHEDRON LETTERS, 1997, 38 (10) :1825-1828

[3] 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

[4] Palladium catalysed cascade bis-cyclisation-anion capture processes proceeding via allenyl-palladium(II) starter species. 1-vinyl-3-azabicyclo[3.1.0]hexanes. [J].

Grigg, R ;

Rasul, R ;

Redpath, J ;

Wilson, D .

TETRAHEDRON LETTERS, 1996, 37 (26) :4609-4612

[5] Palladium-catalyzed regioselective carbonylation of 2,3-dienylamines to alpha-vinylacrylamides [J].

Imada, Y ;

Vasapollo, G ;

Alper, H .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :7982-7983

[6] SYNTHESIS OF DL-SEPTICINE [J].

IWASHITA, T ;

SUZUKI, M ;

KUSUMI, T ;

KAKISAWA, H .

CHEMISTRY LETTERS, 1980, (04) :383-386

[7]

Kiji J, 1997, SYNTHESIS-STUTTGART, P869

[8] EFFICIENT PREPARATION OF POLYSUBSTITUTED 1,3-DIENES FROM ALPHA,ALPHA'-DIKETO SULFIDES [J].

NAKAYAMA, J ;

MACHIDA, H ;

SAITO, R ;

AKIMOTO, K ;

HOSHINO, M .

CHEMISTRY LETTERS, 1985, (08) :1173-1176

[9] PREPARATION OF METHYL 1,3-DIEN-2-CARBOXYLATE BY THE PALLADIUM-CATALYZED CARBONYLATION OF 2,3-DIEN-1-OLS [J].

NOKAMI, J ;

MAIHARA, A ;

TSUJI, J .

TETRAHEDRON LETTERS, 1990, 31 (39) :5629-5630

[10] REACTION OF 2,3-DI(P-ANISYL)-2,3-BUTANEDIOL WITH ACETYL BROMIDE [J].

OGATA, Y ;

KAWASAKI, A ;

HABA, M ;

TSUJINO, T .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (14) :2423-2425