The palladium-catalyzed cross-coupling reaction of 9-organothio-9-borabicyclo[3.3.1]nonanes with organic electrophiles: Synthesis of unsymmetrical sulfides

Ishiyama, Tatsuo; Mori, Masashi; Suzuki, Akira et al.

Journal of Organometallic Chemistry, 1996, 525(1-2), 225-231

Permalink : https://hdl.handle.net/2115/56159

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アクセス権
open access
URI
https://hdl.handle.net/2115/56159
タイトル
The palladium-catalyzed cross-coupling reaction of 9-organothio-9-borabicyclo[3.3.1]nonanes with organic electrophiles: Synthesis of unsymmetrical sulfides
著者
Ishiyama, Tatsuo ; Mori, Masashi ; Suzuki, Akira ; Miyaura, Norio
e-Rad_Researcher
00232348
著者名
Ishiyama, Tatsuo
著者名
Mori, Masashi
e-Rad_Researcher
40001185
著者名
Suzuki, Akira
e-Rad_Researcher
10002049
著者名
Miyaura, Norio
言語
英語
キーワード
Boron
Palladium
発行日
1996-11-15
出版者
Elsevier
収録物名
Journal of Organometallic Chemistry
巻(号)
525(1-2)
ページ
225-231
抄録
The synthesis of unsymmetrical sulfides was carried out in high yields by the palladium-catalyzed cross-coupling reaction of 9-organothio-9-bombicyclo[3.3. l]nonane (9-RS-9-BBN) with organic electrophiles, such as iodoarenes, i-iodo-I-alkenes, allyl carbonate and propargyl carbonate, lodoarenes and I-iodo-l-alkenes were smoothly converted into the corresponding sulfides at 50°C in the presence of PdCi_~(dppO (3 tool%) and K 3PO4 (3 equiv.) in DMF. in contrast, the cross-coupling reaction of 9-RS-9-BBN with allyl or propargyl carbonates occurred in DMF without the assistance of a base. Both reactions ~. :talyzed by Pd(dba)z-dppf regioselectively produced allyl and allenyl sulfides in excellent yields. The scope and limitations of the reactions, as well as the effects of varying the ~action conditions, are discussed.
資源タイプ
学術雑誌論文
出版タイプ
Submitted Manuscript Under Review
PISSN
0022-328X
関連情報 (isVersionOf)
出版社版DOI
https://doi.org/10.1016/S0022-328X(96)06495-9