PALLADIUM(0)-CATALYZED THIOBORATION OF TERMINAL ALKYNES WITH 9-(ALKYLTHIO)-9-BORABICYCLO[3.3.1]NONANE DERIVATIVES - STEREOSELECTIVE SYNTHESIS OF VINYL SULFIDES VIA THE THIOBORATION CROSS-COUPLING SEQUENCE

被引：131

作者：

ISHIYAMA, T ^{[1
]}

NISHIJIMA, K ^{[1
]}

MIYAURA, N ^{[1
]}

SUZUKI, A ^{[1
]}

机构：

[1] HOKKAIDO UNIV,FAC ENGN,DEPT APPL CHEM,SAPPORO,HOKKAIDO 060,JAPAN

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1993年 / 115卷 / 16期

关键词：

D O I：

10.1021/ja00069a020

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The addition of 9-(alkylthio)-9-borabicyclo[3.3.1]nonanes(9-(RS)-9-BBN) 1 to terminal alkynes was catalyzed by Pd(PPh3)4 (3 mol %) to produce 9-[(Z)-2-(alkylthio)-1-alkenyl]-9-BBN derivatives 2 in high yields. The reactions were highly regio- and stereoselective, and their conditions were sufficiently mild that a variety of functionalized alkenylboranes 2 with defined stereochemistry were readily synthesized. The boranes 2 exhibited exceptionally high reactivity on protonolysis with methanol to produce the Markovnikov adducts of thiols to 1-alkynes, 2-(alkylthio)-1-alkenes 3. The synthetic utility of the present reaction was demonstrated by the regio- and stereoselective one-pot synthesis of alkenyl sulfides 7 via the palladium-catalyzed thioboration-cross-coupling sequence.

引用

页码：7219 / 7225

页数：7

共 78 条

[31] ZIRCONIUM-CATALYZED DIENE AND ALKYL ALKENE COUPLING REACTIONS WITH MAGNESIUM REAGENTS [J].

KNIGHT, KS ;

WAYMOUTH, RM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) :6268-6270

[32] SYNTHESIS AND STRUCTURE OF A [(1,2-PHENYLENEDIOXY)BORYL]IRIDIUM HYDRIDE COMPLEX - A MODEL SYSTEM FOR STUDYING CATALYTIC HYDROBORATION [J].

KNORR, JR ;

MEROLA, JS .

ORGANOMETALLICS, 1990, 9 (12) :3008-3010

[33] OXIDATIVE ADDITION OF "4,4,6-TRIMETHYL-1,3,2-DIOXABORINANE AND BENZO[1,3,2]DIOXABOROLE TO TRIS(TRIPHENYLPHOSPHINE) HALOGENORHODIUM [J].

KONO, H ;

ITO, K ;

NAGAI, Y .

CHEMISTRY LETTERS, 1975, (10) :1095-1096

[34] PALLADIUM-CATALYZED ADDITION AND CARBONYLATIVE ADDITION OF DIARYL DISULFIDES AND DISELENIDES TO TERMINAL ACETYLENES [J].

KUNIYASU, H ;

OGAWA, A ;

MIYAZAKI, SI ;

RYU, I ;

KAMBE, N ;

SONODA, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (26) :9796-9803

[35] THE 1ST EXAMPLE OF TRANSITION-METAL-CATALYZED ADDITION OF AROMATIC THIOLS TO ACETYLENES [J].

KUNIYASU, H ;

OGAWA, A ;

SATO, KI ;

RYU, I ;

KAMBE, N ;

SONODA, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) :5902-5903

[36]

LAPPERT MF, 1960, ANGEW CHEM INT EDIT, V72, P36

[37] CATALYTIC HYDROBORATION WITH RHODIUM COMPLEXES [J].

MANNIG, D ;

NOTH, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (10) :878-879

[38] REGIO-SELECTIVE AND STEREO-SELECTIVE SYNTHESIS OF VINYLSTANNANES - TRANSITION-METAL CATALYZED STANNYLMETALATION OF ACETYLENES AND CONVERSION OF ENOL TRIFLATES AND VINYL IODIDES INTO VINYLSTANNANES [J].

MATSUBARA, S ;

HIBINO, JI ;

MORIZAWA, Y ;

OSHIMA, K ;

NOZAKI, H .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 285 (1-3) :163-172

[39] PALLADIUM(0)-CATALYZED HYDROBORATION OF 1-BUTEN-3-YNES - PREPARATION OF ALLENYLBORANES [J].

MATSUMOTO, Y ;

NAITO, M ;

HAYASHI, T .

ORGANOMETALLICS, 1992, 11 (07) :2732-2734

[40]

MIKHAILOV BM, 1974, ZH OBSHCH KHIM+, V44, P2185

← 1 2 3 4 5 6 7 8 →