The chemistry of benzodisilacyclobutenes and benzobis(disilacyclobutene)s

New development of transition-metal-catalyzed reactions, stereochemistry and theoretical studies

Mitsuo Ishikawa, Akinobu Naka, Kazunari Yoshizawa

Research output: Contribution to journalReview article

7 Citations (Scopus)

Abstract

The synthesis and reactions of 3,4-benzo-1,2-disilacyclobut-3-enes and benzo[1,2:4,5]bis(1,2-disilacyclobut-3-ene)s developed by our group are reported in this review. The palladium-, platinum- and nickel-catalyzed reactions of benzodisilacyclobutenes and benzobis(disilacyclobutene)s with unsaturated compounds afford various types of products. The structures of the products are dependent upon the nature of the transition metal used as a catalyst. The reactions of cis- and trans-benzodisilacyclobutenes with alkenes and alkynes in the presence of a transition-metal catalyst proceed with high stereospecificity to give the respective adducts. The thermal reactions of cis- and trans-benzodisilacyclobutenes with various substrates also proceed stereospecifically to give adducts. The results of theoretical calculations for the platinum-catalyzed reaction of disilacyclobutene with acetylene, the nickel-catalyzed reaction of benzodisilacyclobutene and the thermal reaction of benzobis(disilacyclobutene) are discussed in this review.

Original languageEnglish
Pages (from-to)3210-3235
Number of pages26
JournalDalton Transactions
Volume45
Issue number8
DOIs
Publication statusPublished - Jan 1 2016

Fingerprint

Stereochemistry
Platinum
Nickel
Transition metals
Unsaturated compounds
Acetylene
Catalysts
Alkynes
Palladium
Alkenes
Substrates
Hot Temperature

All Science Journal Classification (ASJC) codes

  • Inorganic Chemistry

Cite this

The chemistry of benzodisilacyclobutenes and benzobis(disilacyclobutene)s : New development of transition-metal-catalyzed reactions, stereochemistry and theoretical studies. / Ishikawa, Mitsuo; Naka, Akinobu; Yoshizawa, Kazunari.

In: Dalton Transactions, Vol. 45, No. 8, 01.01.2016, p. 3210-3235.

Research output: Contribution to journalReview article

@article{04be7f3e8b9a4cbe8d3972139c37c847,
title = "The chemistry of benzodisilacyclobutenes and benzobis(disilacyclobutene)s: New development of transition-metal-catalyzed reactions, stereochemistry and theoretical studies",
abstract = "The synthesis and reactions of 3,4-benzo-1,2-disilacyclobut-3-enes and benzo[1,2:4,5]bis(1,2-disilacyclobut-3-ene)s developed by our group are reported in this review. The palladium-, platinum- and nickel-catalyzed reactions of benzodisilacyclobutenes and benzobis(disilacyclobutene)s with unsaturated compounds afford various types of products. The structures of the products are dependent upon the nature of the transition metal used as a catalyst. The reactions of cis- and trans-benzodisilacyclobutenes with alkenes and alkynes in the presence of a transition-metal catalyst proceed with high stereospecificity to give the respective adducts. The thermal reactions of cis- and trans-benzodisilacyclobutenes with various substrates also proceed stereospecifically to give adducts. The results of theoretical calculations for the platinum-catalyzed reaction of disilacyclobutene with acetylene, the nickel-catalyzed reaction of benzodisilacyclobutene and the thermal reaction of benzobis(disilacyclobutene) are discussed in this review.",
author = "Mitsuo Ishikawa and Akinobu Naka and Kazunari Yoshizawa",
year = "2016",
month = "1",
day = "1",
doi = "10.1039/c5dt04569j",
language = "English",
volume = "45",
pages = "3210--3235",
journal = "Dalton Transactions",
issn = "1477-9226",
publisher = "Royal Society of Chemistry",
number = "8",

}

TY - JOUR

T1 - The chemistry of benzodisilacyclobutenes and benzobis(disilacyclobutene)s

T2 - New development of transition-metal-catalyzed reactions, stereochemistry and theoretical studies

AU - Ishikawa, Mitsuo

AU - Naka, Akinobu

AU - Yoshizawa, Kazunari

PY - 2016/1/1

Y1 - 2016/1/1

N2 - The synthesis and reactions of 3,4-benzo-1,2-disilacyclobut-3-enes and benzo[1,2:4,5]bis(1,2-disilacyclobut-3-ene)s developed by our group are reported in this review. The palladium-, platinum- and nickel-catalyzed reactions of benzodisilacyclobutenes and benzobis(disilacyclobutene)s with unsaturated compounds afford various types of products. The structures of the products are dependent upon the nature of the transition metal used as a catalyst. The reactions of cis- and trans-benzodisilacyclobutenes with alkenes and alkynes in the presence of a transition-metal catalyst proceed with high stereospecificity to give the respective adducts. The thermal reactions of cis- and trans-benzodisilacyclobutenes with various substrates also proceed stereospecifically to give adducts. The results of theoretical calculations for the platinum-catalyzed reaction of disilacyclobutene with acetylene, the nickel-catalyzed reaction of benzodisilacyclobutene and the thermal reaction of benzobis(disilacyclobutene) are discussed in this review.

AB - The synthesis and reactions of 3,4-benzo-1,2-disilacyclobut-3-enes and benzo[1,2:4,5]bis(1,2-disilacyclobut-3-ene)s developed by our group are reported in this review. The palladium-, platinum- and nickel-catalyzed reactions of benzodisilacyclobutenes and benzobis(disilacyclobutene)s with unsaturated compounds afford various types of products. The structures of the products are dependent upon the nature of the transition metal used as a catalyst. The reactions of cis- and trans-benzodisilacyclobutenes with alkenes and alkynes in the presence of a transition-metal catalyst proceed with high stereospecificity to give the respective adducts. The thermal reactions of cis- and trans-benzodisilacyclobutenes with various substrates also proceed stereospecifically to give adducts. The results of theoretical calculations for the platinum-catalyzed reaction of disilacyclobutene with acetylene, the nickel-catalyzed reaction of benzodisilacyclobutene and the thermal reaction of benzobis(disilacyclobutene) are discussed in this review.

UR - http://www.scopus.com/inward/record.url?scp=84959191540&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84959191540&partnerID=8YFLogxK

U2 - 10.1039/c5dt04569j

DO - 10.1039/c5dt04569j

M3 - Review article

VL - 45

SP - 3210

EP - 3235

JO - Dalton Transactions

JF - Dalton Transactions

SN - 1477-9226

IS - 8

ER -