Photochemical Formation of Dibenzosilacyclohept-4-yne for
Cu-Free Click Chemistry with Azides and 1,2,4,5-Tetrazines

J 2016

Photochemical Formation of Dibenzosilacyclohept-4-yne for Cu-Free Click Chemistry with Azides and 1,2,4,5-Tetrazines

MARTÍNEK, Marek, Lenka FILIPOVÁ, Juraj GALETA, Lucie LUDVÍKOVÁ, Petr KLÁN et. al.

Basic information

Original name

Photochemical Formation of Dibenzosilacyclohept-4-yne for Cu-Free Click Chemistry with Azides and 1,2,4,5-Tetrazines

Authors

MARTÍNEK, Marek (203 Czech Republic, belonging to the institution), Lenka FILIPOVÁ (203 Czech Republic, belonging to the institution), Juraj GALETA (703 Slovakia, belonging to the institution), Lucie LUDVÍKOVÁ (203 Czech Republic, belonging to the institution) and Petr KLÁN (203 Czech Republic, guarantor, belonging to the institution)

Edition

Organic Letters, WASHINGTON, American Chemical Society, 2016, 1523-7060

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 6.579

RIV identification code

RIV/00216224:14310/16:00088609

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1021/acs.orglett.6b02367

UT WoS

000385053900035

Keywords in English

DIELS-ALDER REACTIONS; CYCLOADDITION REACTIONS; BIOORTHOGONAL REACTIONS; LIVING CELLS; GENERATION; REACTIVITY; SIEBENRINGSYSTEMEN; BIOCONJUGATION; CYCLOHEPTYNES; BIOMOLECULES

Abstract

V originále

Photochemical generation of dibeniOsilacyclohept-4-yne 3 from the corresponding, cydopropenone 1 and its copper-free click reactions are reported. Steady-state irradiation, kinetic, and- transient absorption spectroscopy studies revealed that strained alkyne 3 is rapidly (<5 ns) and efficiently (Phi = 0.58-0.71) photoreleased from 1 and undergoes remarkably fast, selective, and high-yielding 1,3-dipolar cycloaddition with benzyl azide (similar to 20 M-1 s(-1)) or [4 + 2] inverse electron-demand Diels Alder reaction with 1,2,4,5-tetrazines (similar to 260 M-1 s(-1)) in both methanol and acetonitrile.

Links

GA13-25775S, research and development project

Name: Vývoj viditelným světlem aktivovatelných skupin a fluorescenčních značek pro chemii a biologii

Investor: Czech Science Foundation

LM2015051, research and development project

Name: Centrum pro výzkum toxických látek v prostředí (Acronym: RECETOX RI)

Investor: Ministry of Education, Youth and Sports of the CR

LO1214, research and development project

Name: Centrum pro výzkum toxických látek v prostředí (Acronym: RECETOX)

Investor: Ministry of Education, Youth and Sports of the CR

Citovat

MARTÍNEK, Marek, Lenka FILIPOVÁ, Juraj GALETA, Lucie LUDVÍKOVÁ and Petr KLÁN. Photochemical Formation of Dibenzosilacyclohept-4-yne for Cu-Free Click Chemistry with Azides and 1,2,4,5-Tetrazines. Organic Letters. WASHINGTON: American Chemical Society, 2016, vol. 18, No 19, p. 4892-4895. ISSN 1523-7060. Available from: https://dx.doi.org/10.1021/acs.orglett.6b02367.

@article{1369915,
   author = {Martínek, Marek and Filipová, Lenka and Galeta, Juraj and Ludvíková, Lucie and Klán, Petr},
   article_location = {WASHINGTON},
   article_number = {19},
   doi = {http://dx.doi.org/10.1021/acs.orglett.6b02367},
   keywords = {DIELS-ALDER REACTIONS; CYCLOADDITION REACTIONS; BIOORTHOGONAL REACTIONS; LIVING CELLS; GENERATION; REACTIVITY; SIEBENRINGSYSTEMEN; BIOCONJUGATION; CYCLOHEPTYNES; BIOMOLECULES},
   language = {eng},
   issn = {1523-7060},
   journal = {Organic Letters},
   title = {Photochemical Formation of Dibenzosilacyclohept-4-yne for Cu-Free Click Chemistry with Azides and 1,2,4,5-Tetrazines},
   url = {http://pubs.acs.org/doi/abs/10.1021/acs.orglett.6b02367},
   volume = {18},
   year = {2016}
}

TY  - JOUR
ID  - 1369915
AU  - Martínek, Marek - Filipová, Lenka - Galeta, Juraj - Ludvíková, Lucie - Klán, Petr
PY  - 2016
TI  - Photochemical Formation of Dibenzosilacyclohept-4-yne for Cu-Free Click Chemistry with Azides and 1,2,4,5-Tetrazines
JF  - Organic Letters
VL  - 18
IS  - 19
SP  - 4892-4895
EP  - 4892-4895
PB  - American Chemical Society
SN  - 15237060
KW  - DIELS-ALDER REACTIONS
KW  - CYCLOADDITION REACTIONS
KW  - BIOORTHOGONAL REACTIONS
KW  - LIVING CELLS
KW  - GENERATION
KW  - REACTIVITY
KW  - SIEBENRINGSYSTEMEN
KW  - BIOCONJUGATION
KW  - CYCLOHEPTYNES
KW  - BIOMOLECULES
UR  - http://pubs.acs.org/doi/abs/10.1021/acs.orglett.6b02367
L2  - http://pubs.acs.org/doi/abs/10.1021/acs.orglett.6b02367
N2  - Photochemical generation of dibeniOsilacyclohept-4-yne 3 from the corresponding, cydopropenone 1 and its copper-free click reactions are reported. Steady-state irradiation, kinetic, and- transient absorption spectroscopy studies revealed that strained alkyne 3 is rapidly (<5 ns) and efficiently (Phi = 0.58-0.71) photoreleased from 1 and undergoes remarkably fast, selective, and high-yielding 1,3-dipolar cycloaddition with benzyl azide (similar to 20 M-1 s(-1)) or [4 + 2] inverse electron-demand Diels Alder reaction with 1,2,4,5-tetrazines (similar to 260 M-1 s(-1)) in both methanol and acetonitrile.
ER  -

MARTÍNEK, Marek, Lenka FILIPOVÁ, Juraj GALETA, Lucie LUDVÍKOVÁ and Petr KLÁN. Photochemical Formation of Dibenzosilacyclohept-4-yne for Cu-Free Click Chemistry with Azides and 1,2,4,5-Tetrazines. \textit{Organic Letters}. WASHINGTON: American Chemical Society, 2016, vol.~18, No~19, p.~4892-4895. ISSN~1523-7060. Available from: https://dx.doi.org/10.1021/acs.orglett.6b02367.

Detailed Information on Publication Record