Diboryldiborenes: π-Conjugated B4 Chains Isoelectronic to the Butadiene Dication

Alexander Hermann; Jessica Cid; James D. Mattock; Rian D. Dewhurst; Ivo Krummenacher; Alfredo Vargas; Michael J. Ingleson; Holger Braunschweig

doi:10.1002/anie.201805394

Diboryldiborenes: π-Conjugated B4 Chains Isoelectronic to the Butadiene Dication

Alexander Hermann, Jessica Cid, James D. Mattock, Rian D. Dewhurst, Ivo Krummenacher, Alfredo Vargas^*, Michael J. Ingleson, Holger Braunschweig

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

B(sp²)–B(sp³) diborane species based on bis(catecholato)diboron and N-heterocyclic carbenes (NHCs) underwent catechol/bromide exchange selectively at the sp³-hybridized boron atom. The reduction of the resulting 1,1-dibromodiborane adducts led to reductive coupling and isolation of doubly NHC-stabilized 1,2-diboryldiborenes. These compounds are the first examples of molecules exhibiting π-electron delocalization over an all-boron chain.

Original language	English
Pages (from-to)	10091-10095
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	57
Issue number	32
Early online date	15 Jul 2018
DOIs	https://doi.org/10.1002/anie.201805394
Publication status	Published - 6 Aug 2018

Keywords / Materials (for Non-textual outputs)

boron chains
diboranes
diborenes
N-heterocyclic carbenes
π-conjugation

Access to Document

10.1002/anie.201805394

https://www.research.manchester.ac.uk/portal/en/publications/diboryldiborenes-conjugated-b4-chains-isoelectronic-to-the-butadiene-dication(2bd403ff-49b0-4bb1-973a-2da9a4f531f3).html

Michael Ingleson
- School of Chemistry - Personal Chair of Inorganic Chemistry
- EaStCHEM
Person: Academic: Research Active

Cite this

@article{662f557dab584c7aa6976ff50752f7d7,

title = "Diboryldiborenes: π-Conjugated B4 Chains Isoelectronic to the Butadiene Dication",

abstract = "B(sp2)–B(sp3) diborane species based on bis(catecholato)diboron and N-heterocyclic carbenes (NHCs) underwent catechol/bromide exchange selectively at the sp3-hybridized boron atom. The reduction of the resulting 1,1-dibromodiborane adducts led to reductive coupling and isolation of doubly NHC-stabilized 1,2-diboryldiborenes. These compounds are the first examples of molecules exhibiting π-electron delocalization over an all-boron chain.",

keywords = "boron chains, diboranes, diborenes, N-heterocyclic carbenes, π-conjugation",

author = "Alexander Hermann and Jessica Cid and Mattock, \{James D.\} and Dewhurst, \{Rian D.\} and Ivo Krummenacher and Alfredo Vargas and Ingleson, \{Michael J.\} and Holger Braunschweig",

note = "Date of acceptance not shown on journal site. Used AAM online date (knowing Angewandte usually outs AAMs online immediately), in order to allow application of exception. MI joined Edinburgh in April 2019.",

year = "2018",

month = aug,

day = "6",

doi = "10.1002/anie.201805394",

language = "English",

volume = "57",

pages = "10091--10095",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "Wiley",

number = "32",

}

TY - JOUR

T1 - Diboryldiborenes: π-Conjugated B4 Chains Isoelectronic to the Butadiene Dication

AU - Hermann, Alexander

AU - Cid, Jessica

AU - Mattock, James D.

AU - Dewhurst, Rian D.

AU - Krummenacher, Ivo

AU - Vargas, Alfredo

AU - Ingleson, Michael J.

AU - Braunschweig, Holger

N1 - Date of acceptance not shown on journal site. Used AAM online date (knowing Angewandte usually outs AAMs online immediately), in order to allow application of exception. MI joined Edinburgh in April 2019.

PY - 2018/8/6

Y1 - 2018/8/6

N2 - B(sp2)–B(sp3) diborane species based on bis(catecholato)diboron and N-heterocyclic carbenes (NHCs) underwent catechol/bromide exchange selectively at the sp3-hybridized boron atom. The reduction of the resulting 1,1-dibromodiborane adducts led to reductive coupling and isolation of doubly NHC-stabilized 1,2-diboryldiborenes. These compounds are the first examples of molecules exhibiting π-electron delocalization over an all-boron chain.

AB - B(sp2)–B(sp3) diborane species based on bis(catecholato)diboron and N-heterocyclic carbenes (NHCs) underwent catechol/bromide exchange selectively at the sp3-hybridized boron atom. The reduction of the resulting 1,1-dibromodiborane adducts led to reductive coupling and isolation of doubly NHC-stabilized 1,2-diboryldiborenes. These compounds are the first examples of molecules exhibiting π-electron delocalization over an all-boron chain.

KW - boron chains

KW - diboranes

KW - diborenes

KW - N-heterocyclic carbenes

KW - π-conjugation

U2 - 10.1002/anie.201805394

DO - 10.1002/anie.201805394

M3 - Article

C2 - 29897648

AN - SCOPUS:85050797522

SN - 1433-7851

VL - 57

SP - 10091

EP - 10095

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 32

ER -

Diboryldiborenes: π-Conjugated B4 Chains Isoelectronic to the Butadiene Dication

Abstract

Keywords / Materials (for Non-textual outputs)

Access to Document

Fingerprint

Profiles

Michael Ingleson

Cite this