2018
DOI: 10.1002/anie.201801031
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One‐Pot Sequence‐Controlled Synthesis of Oligosiloxanes

Kazuhiro Matsumoto,
Yuki Oba,
Yumiko Nakajima
et al.

Abstract: Silicones (organopolysiloxanes) have found applications in a wide range of research areas, and their unique and valuable properties have rendered these materials virtually irreplaceable. Despite the fact that silicones have been employed industrially for more than 70 years, synthetic routes to generate silicones remain limited, and the sequence-controlled synthesis of oligo- and polysiloxanes still represents a major challenge in silicone chemistry. Described here is a highly selective sequence-controlled synt… Show more

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Cited by 56 publications
(41 citation statements)
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“…Current challenges include tackling the development of simpler and greener alternatives to traditional synthetic methods while retaining the benefits of controlled living polymerization. [43] By virtue of multiple (up to 9) sequential one-pot additions of hydrosilane and carbonyl compounds,o ligo-linear,b ranched, and cyclic polysiloxanes can be obtained with moderate yields (> 40 %). [36] Polycondensation reactions that offer new reaction pathways and sophisticated sequence control are also searched for.…”
Section: Angewandte Chemiementioning
confidence: 99%
“…Current challenges include tackling the development of simpler and greener alternatives to traditional synthetic methods while retaining the benefits of controlled living polymerization. [43] By virtue of multiple (up to 9) sequential one-pot additions of hydrosilane and carbonyl compounds,o ligo-linear,b ranched, and cyclic polysiloxanes can be obtained with moderate yields (> 40 %). [36] Polycondensation reactions that offer new reaction pathways and sophisticated sequence control are also searched for.…”
Section: Angewandte Chemiementioning
confidence: 99%
“…So konnten beispielsweise starke organische Basen, insbesondere Guanidine,d ie lebende ROPv on Cyclooligosiloxanen mit Wasser als Initiator katalysieren und Polymere mit engen Dispersitäten von < 1.2, hohen M n -Werten und Umsätzen sowie hoher Genauigkeit bei der Endgruppenschützenden Funktionalisierung liefern (25;S chema 4a). [43] Durch mehrfache (bis zu neun) aufeinanderfolgende Ein-Topf-Zugaben von Hydrosilan-und Carbonyl-Verbindungen kçnnen oligo-lineare,verzweigte und cyclische Polysiloxane in moderaten Ausbeuten (> 40 %) erhalten werden. In diesem Zusammenhang zeichnet sich B(C 6 F 5 ) 3 als leistungsfähiger Organokatalysator aus.…”
Section: Polysiloxaneunclassified
“…Scheme illustrates a representative example for the one‐pot controlled iteration of the Piers–Rubinsztajn reaction and B(C 6 F 5 ) 3 ‐catalyzed hydrosilylation, affording the sequence‐specific pentasiloxane Me 3 SiOSiPh 2 OSiEt 2 OSiPh 2 OSiEt 2 H ( 8 ), through four continuous siloxane‐bond elongations . Initially, alkoxysilane 1 reacted with Ph 2 SiH 2 , catalyzed by B(C 6 F 5 ) 3 , to give disiloxane 2 , which contained a Si−H moiety.…”
Section: One‐pot Iterative Synthesis Of Sequence‐ Specific Oligosiloxmentioning
confidence: 99%
“…Scheme12i llustrates ar epresentative example for the onepot controlled iteration of the Piers-Rubinsztajn reactiona nd B(C 6 F 5 ) 3 -catalyzed hydrosilylation, affording the sequence-specific pentasiloxane Me 3 SiOSiPh 2 OSiEt 2 OSiPh 2 OSiEt 2 H( 8), throughf our continuous siloxane-bond elongations. [42] Initially, alkoxysilane 1 reacted withP h 2 SiH 2 ,c atalyzed by B(C 6 F 5 ) 3 ,t o give disiloxane 2,w hichc ontained aS i ÀHm oiety.T he addition of acetone to the reaction mixture after completion of the first reaction induced B(C 6 F 5 ) 3 -catalyzed hydrosilylation at the SiÀH group. Because the as-obtained disiloxane (3)c ontained aS i À OiPr group, compound 3 underwent the second Piers-Rubinsztajn reactionw ith Et 2 SiH 2 to afford trisiloxane 4 in as equencecontrolled manner.…”
Section: One-pot Iterative Synthesis Of Sequence-specific Oligosiloxanesmentioning
confidence: 99%