Amidoximes provide facile platinum(II)-mediated oxime-nitrile coupling

Inorganic Chemistry
Dmitrii S BolotinVadim Yu Kukushkin

Abstract

The nucleophilic addition of amidoximes R'C(NH(2))═NOH [R' = Me (2.Me), Ph (2.Ph)] to coordinated nitriles in the platinum(II) complexes trans-[PtCl(2)(RCN)(2)] [R = Et (1t.Et), Ph (1t.Ph), NMe(2) (1t.NMe(2))] and cis-[PtCl(2)(RCN)(2)] [R = Et (1c.Et), Ph (1c.Ph), NMe(2) (1c.NMe(2))] proceeds in a 1:1 molar ratio and leads to the monoaddition products trans-[PtCl(RCN){HN═C(R)ONC(R')NH(2)}]Cl [R = NMe(2); R' = Me ([3a]Cl), Ph ([3b]Cl)], cis-[PtCl(2){HN═C(R)ONC(R')NH(2)}] [R = NMe(2); R' = Me (4a), Ph (4b)], and trans/cis-[PtCl(2)(RCN){HN═C(R)ONC(R')NH(2)}] [R = Et; R' = Me (5a, 6a), Ph (5b, 6b); R = Ph; R' = Me (5c, 6c), Ph (5d, 6d), correspondingly]. If the nucleophilic addition proceeds in a 2:1 molar ratio, the reaction gives the bisaddition species trans/cis-[Pt{HN═C(R)ONC(R')NH(2)}(2)]Cl(2) [R = NMe(2); R' = Me ([7a]Cl(2), [8a]Cl(2)), Ph ([7b]Cl(2), [8b]Cl(2))] and trans/cis-[PtCl(2){HN═C(R)ONC(R')NH(2)}(2)] [R = Et; R' = Me (10a), Ph (9b, 10b); R = Ph; R' = Me (9c, 10c), Ph (9d, 10d), respectively]. The reaction of 1 equiv of the corresponding amidoxime and each of [3a]Cl, [3b]Cl, 5b-5d, and 6a-6d leads to [7a]Cl(2), [7b]Cl(2), 9b-9d, and 10a-10d. Open-chain bisaddition species 9b-9d and 10a-10d were transformed to corresp...Continue Reading

References

Oct 24, 2001·Inorganic Chemistry·Vadim Yu. KukushkinArmando J. L. Pombeiro
May 9, 2002·Chemical Reviews·Vadim Yu Kukushkin, Armando J L Pombeiro
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Citations

Nov 20, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·Vivek GuptaGanapathi Anantharaman
Sep 17, 2013·Chemistry : a European Journal·Maialen Espinal ViguriLucía Riera
Sep 16, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·Andrey S SmirnovVadim Yu Kukushkin
Oct 17, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Antonio Abellán-LópezJosé Vicente
Jul 22, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Zarina M BikbaevaVadim Yu Kukushkin
Mar 31, 2015·Inorganic Chemistry·Dmitrii S BolotinVadim Yu Kukushkin
Oct 11, 2017·Chemical Reviews·Dmitrii S BolotinVadim Yu Kukushkin

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