Super-electron donors: Bis-pyridinylidene formation by base treatment of pyridinium salts

Super-electron donors: Bis-pyridinylidene formation by base treatment of pyridinium salts
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DOI:
10.1021/ol800134g
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发表时间:
2008-03-20
期刊:
影响因子:
5.2
通讯作者:
Turner, Andrew T.
Turner, Andrew T.
中科院分区:
化学1区
文献类型:
--
作者:
Murphy, John A.;Garnier, Jean;Turner, Andrew T.

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双吡啶盐7b的去质子化得到了双吡啶10,一个非常强大的中性有机双电子给体[E(1/2)(DMF)=-1.13V vs Ag/AgCl/KCl(Sat)],推测是通过吡啶8来实现的。给体10以极高的产率将芳基碘和溴化物还原为芳基阴离子,并非常有效地还原裂解选定的苯基烷基砜。
Deprotonation of bispyridinium salt 7b affords bispyridinylidene 10, a very powerful neutral organic two-electron donor [E(1/2) (DMF)=-1.13 V vs Ag/AgCl/KCl (sat)], presumably via the pyridinylidene 8. Donor 10 reduces aryl iodides and bromides to aryl anions in excellent yield and also reductively cleaves selected phenylalkylsulfones very efficiently.