引用本文:
Ye Qian Wen, Wei Min Ren, Xiao Bing Lu. Highly active bifunctional salenTi(IV) catalysts for asymmetric cyanosilylation of aldehydes and TMSCN[J]. Chinese Chemical Letters,
2011, 22(11): 1285-1288.
doi:
10.1016/j.cclet.2011.06.016
Citation: Ye Qian Wen, Wei Min Ren, Xiao Bing Lu. Highly active bifunctional salenTi(IV) catalysts for asymmetric cyanosilylation of aldehydes and TMSCN[J]. Chinese Chemical Letters, 2011, 22(11): 1285-1288. doi: 10.1016/j.cclet.2011.06.016
Citation: Ye Qian Wen, Wei Min Ren, Xiao Bing Lu. Highly active bifunctional salenTi(IV) catalysts for asymmetric cyanosilylation of aldehydes and TMSCN[J]. Chinese Chemical Letters, 2011, 22(11): 1285-1288. doi: 10.1016/j.cclet.2011.06.016
Highly active bifunctional salenTi(IV) catalysts for asymmetric cyanosilylation of aldehydes and TMSCN
摘要:
A novel enantiopure salen ligand bearing a diphenylphosphine oxide on the 3-position of one aromatic ring was synthesized and combined with Ti (Oi-Pr)4 as a monometallic bifunctional catalyst for asymmetric cyanosilylation reaction of aldehydes with trimethylsilyl cyanide (TMSCN). The catalyst system exhibited excellent activity and moderate enantioselectivity. The addition of TMSCN to 4-nitrobenzaldehyde in the presence of 1 mol% catalyst loading could complete within 10 min at ambient temperature. An intramolecularly cooperative catalysis was observed in this system wherein the central metal Ti (IV) is suggested to play a role of Lewis acid to activate aldehydes while the appended diphenylphosphine oxide worked as Lewis base to activate TMSCN.
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关键词:
- Cyanohydrin
- / Bifunctional catalyst
- / Salen
- / TMSCN
- / Diphenylphosphine oxide
English
Highly active bifunctional salenTi(IV) catalysts for asymmetric cyanosilylation of aldehydes and TMSCN
Abstract:
A novel enantiopure salen ligand bearing a diphenylphosphine oxide on the 3-position of one aromatic ring was synthesized and combined with Ti(Oi-Pr)4 as a monometallic bifunctional catalyst for asymmetric cyanosilylation reaction of aldehydes with trimethylsilyl cyanide (TMSCN). The catalyst system exhibited excellent activity and moderate enantioselectivity. The addition of TMSCN to 4-nitrobenzaldehyde in the presence of 1 mol% catalyst loading could complete within 10 min at ambient temperature. An intramolecularly cooperative catalysis was observed in this system wherein the central metal Ti(IV) is suggested to play a role of Lewis acid to activate aldehydes while the appended diphenylphosphine oxide worked as Lewis base to activate TMSCN.
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Key words:
- Cyanohydrin
- / Bifunctional catalyst
- / Salen
- / TMSCN
- / Diphenylphosphine oxide
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