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 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, vol. 18, No 19, p. 4892-4895. ISSN 1523-7060. doi:10.1021/acs.orglett.6b02367. 2016.

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

• Original language: English
• Type of outcome: Article in a journal
• Field of Study: 10401 Organic chemistry
• Country of publisher: United States of America
• Confidentiality degree: is not subject to a state or trade secret
• WWW: 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
• Tags: AKR, rivok
• Tags: International impact, Reviewed

Abstract

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