1,1-hydroboration and a borane adduct of diphenyldiazomethane: a potential prelude to FLP-N2 chemistry

Connie Tang; Quiming Liang; Andrew R. Jupp; Timothy C. Johnstone; Rebecca C. Neu; Datong Song; Stefan Grimme; Douglas W. Stephan

doi:10.1002/anie.201710337

1,1-hydroboration and a borane adduct of diphenyldiazomethane: a potential prelude to FLP-N2 chemistry

Connie Tang, Quiming Liang, Andrew R. Jupp, Timothy C. Johnstone, Rebecca C. Neu, Datong Song, Stefan Grimme, Douglas W. Stephan

Chemistry

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

44 Citations (Scopus)

Abstract

Diphenyldiazomethane reacts with HB(C₆F₅)₂ and B(C₆F₅)₃, resulting in 1,1‐hydroboration and adduct formation, respectively. The hydroboration proceeds via a concerted reaction involving initial formation of the Lewis adduct Ph₂CN₂BH(C₆F₅)₂. The highly sensitive adduct Ph₂CN₂(B(C₆F₅)₃) liberates N₂ and generates Ph₂CB(C₆F₅)₃. DFT computations reveal that formation of Ph₂CN₂B(C₆F₅)₃ from carbene, N₂, and borane is thermodynamically favourable, suggesting steric frustration could preclude carbene–borane adduct formation and affect FLP‐N₂ capture.

Original language	English
Pages (from-to)	16588-16592
Number of pages	5
Journal	Angewandte Chemie (International Edition)
Volume	56
Issue number	52
Early online date	6 Nov 2017
DOIs	https://doi.org/10.1002/anie.201710337
Publication status	Published - 22 Dec 2017

Keywords

adducts
boranes
diphenyldiazomethane
hydroboration
nitrogen

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@article{1817c3f1cef24559bd0cb2c4acdb337e,

title = "1,1-hydroboration and a borane adduct of diphenyldiazomethane: a potential prelude to FLP-N2 chemistry",

abstract = "Diphenyldiazomethane reacts with HB(C6F5)2 and B(C6F5)3, resulting in 1,1‐hydroboration and adduct formation, respectively. The hydroboration proceeds via a concerted reaction involving initial formation of the Lewis adduct Ph2CN2BH(C6F5)2. The highly sensitive adduct Ph2CN2(B(C6F5)3) liberates N2 and generates Ph2CB(C6F5)3. DFT computations reveal that formation of Ph2CN2B(C6F5)3 from carbene, N2, and borane is thermodynamically favourable, suggesting steric frustration could preclude carbene–borane adduct formation and affect FLP‐N2 capture.",

keywords = "adducts, boranes, diphenyldiazomethane, hydroboration, nitrogen",

author = "Connie Tang and Quiming Liang and Jupp, {Andrew R.} and Johnstone, {Timothy C.} and Neu, {Rebecca C.} and Datong Song and Stefan Grimme and Stephan, {Douglas W.}",

year = "2017",

month = dec,

day = "22",

doi = "10.1002/anie.201710337",

language = "English",

volume = "56",

pages = "16588--16592",

journal = "Angewandte Chemie (International Edition) ",

issn = "1433-7851",

publisher = "Wiley-VCH Verlag",

number = "52",

}

TY - JOUR

T1 - 1,1-hydroboration and a borane adduct of diphenyldiazomethane

T2 - a potential prelude to FLP-N2 chemistry

AU - Tang, Connie

AU - Liang, Quiming

AU - Jupp, Andrew R.

AU - Johnstone, Timothy C.

AU - Neu, Rebecca C.

AU - Song, Datong

AU - Grimme, Stefan

AU - Stephan, Douglas W.

PY - 2017/12/22

Y1 - 2017/12/22

N2 - Diphenyldiazomethane reacts with HB(C6F5)2 and B(C6F5)3, resulting in 1,1‐hydroboration and adduct formation, respectively. The hydroboration proceeds via a concerted reaction involving initial formation of the Lewis adduct Ph2CN2BH(C6F5)2. The highly sensitive adduct Ph2CN2(B(C6F5)3) liberates N2 and generates Ph2CB(C6F5)3. DFT computations reveal that formation of Ph2CN2B(C6F5)3 from carbene, N2, and borane is thermodynamically favourable, suggesting steric frustration could preclude carbene–borane adduct formation and affect FLP‐N2 capture.

AB - Diphenyldiazomethane reacts with HB(C6F5)2 and B(C6F5)3, resulting in 1,1‐hydroboration and adduct formation, respectively. The hydroboration proceeds via a concerted reaction involving initial formation of the Lewis adduct Ph2CN2BH(C6F5)2. The highly sensitive adduct Ph2CN2(B(C6F5)3) liberates N2 and generates Ph2CB(C6F5)3. DFT computations reveal that formation of Ph2CN2B(C6F5)3 from carbene, N2, and borane is thermodynamically favourable, suggesting steric frustration could preclude carbene–borane adduct formation and affect FLP‐N2 capture.

KW - adducts

KW - boranes

KW - diphenyldiazomethane

KW - hydroboration

KW - nitrogen

U2 - 10.1002/anie.201710337

DO - 10.1002/anie.201710337

M3 - Article

SN - 1433-7851

VL - 56

SP - 16588

EP - 16592

JO - Angewandte Chemie (International Edition)

JF - Angewandte Chemie (International Edition)

IS - 52

ER -

1,1-hydroboration and a borane adduct of diphenyldiazomethane: a potential prelude to FLP-N2 chemistry

Abstract

Keywords

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