e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Palladium-catalyzed inter-and intramolecular cross-coupling reactions of B-alkyl-9-borabicyclo [3.3. 1] nonane derivatives with 1-halo-1-alkenes or haloarenes. …

…, T Ishiyama, H Sasaki, M Ishikawa, M Sato…

Index: Miyaura, Norio; Ishiyama, Tatsuo; Sasaki, Hirotomo; Ishikawa, Masako; Satoh, Makoto; Suzuki, Akira Journal of the American Chemical Society, 1989 , vol. 111, # 1 p. 314 - 321

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Citation Number: 518

Abstract

Abstract: The cross-coupling reaction of B-alkyl-9-borabicyclo [3.3. l] nonanes (BR-9-BBN), readily obtainable from alkenes by hydroboration, with 1-halo-1-alkenes or haloarenes in the presence of a catalytic amount of PdCl,(dppf) and bases, such as sodium hydroxide, potassium carbonate, and phosphate, gave the corresponding alkenes or arenes. Because the reaction is tolerant of a variety of functionalities on either coupling partner, ...

Methyl 4-iodobenzoate Structure

Methyl 4-iodobe...

methyl 11-(9-borabicyclo[3.3.1]nonan-9-yl)undecanoate Structure

methyl 11-(9-bo...

~84%

methyl 4-(11-methoxy-11-oxoundecyl)benzoate Structure

methyl 4-(11-me...

Methyl undecenate Structure

Methyl undecenate

Methyl 4-iodobenzoate Structure

Methyl 4-iodobe...

~%

methyl 4-(11-methoxy-11-oxoundecyl)benzoate Structure

methyl 4-(11-me...

1-Allyl-2-bromobenzene Structure

1-Allyl-2-bromo...

9-Borabicyclo[3.3.1]nonane Structure

9-Borabicyclo[3...

~85%

Indane Structure

1-Allyl-2-bromobenzene Structure

1-Allyl-2-bromo...

~%

Indane Structure

9-octyl-BBN Structure

Benzene, [(1E)-2-bromoethenyl]- Structure

Benzene, [(1E)-...

~86%

[(E)-dec-1-enyl]benzene Structure

[(E)-dec-1-enyl...

9-octyl-BBN Structure

2-phenylvinyl iodide Structure

2-phenylvinyl iodide

~81%

[(E)-dec-1-enyl]benzene Structure

[(E)-dec-1-enyl...

octene Structure

(2-Bromovinyl)benzene Structure

(2-Bromovinyl)b...

~%

(Z)-1-phenyl-1-decene Structure

(Z)-1-phenyl-1-...

[(E)-dec-1-enyl]benzene Structure

[(E)-dec-1-enyl...

octene Structure

2-phenylvinyl iodide Structure

2-phenylvinyl iodide

~%

(Z)-1-phenyl-1-decene Structure

(Z)-1-phenyl-1-...

[(E)-dec-1-enyl]benzene Structure

[(E)-dec-1-enyl...

Methyl 4-iodobenzoate Structure

Methyl 4-iodobe...

9-methyl-9-borabicyclo [2.2.1]nonane Structure

9-methyl-9-bora...

~78%

methyl p-toluate Structure

methyl p-toluate

9-octyl-BBN Structure

Iodobenzene Structure

~98%

1-Phenyloctane Structure

Iodobenzene Structure

8,8-dicyclohexyloctylboron Structure

8,8-dicyclohexy...

~95%

1-Phenyloctane Structure

Iodobenzene Structure

octyldisiamylborane Structure

octyldisiamylborane

~83%

1-Phenyloctane Structure

9-octyl-BBN Structure

Isocrotyl bromide Structure

Isocrotyl bromide

~98%

2-METHYL-2-UNDECENE Structure

2-METHYL-2-UNDECENE

Isocrotyl bromide Structure

Isocrotyl bromide

octene Structure

~%

2-METHYL-2-UNDECENE Structure

2-METHYL-2-UNDECENE

4-(2-BROMOPHENYL)-1-BUTENE Structure

4-(2-BROMOPHENY...

9-Borabicyclo[3.3.1]nonane Structure

9-Borabicyclo[3...

~64%

1,2,3,4-Tetrahydronaphthalene Structure

1,2,3,4-Tetrahy...

9-(2-methylpropyl)-9-borabicyclo[3.3.1]nonane Structure

9-(2-methylprop...

1-Bromonaphthalene Structure

1-Bromonaphthalene

~87%

1-Isobutylnaphthalene Structure

1-Isobutylnapht...

1-Bromonaphthalene Structure

1-Bromonaphthalene

Isobutylene Structure

~%

1-Isobutylnaphthalene Structure

1-Isobutylnapht...