Bis(imido)vanadium(V)-Catalyzed [2+2+1] Coupling of Alkynes and Azobenzenes Giving Multisubstituted Pyrroles

Kento Kawakita; Evan P. Beaumier; Yuya Kakiuchi; Hayato Tsurugi; Ian A. Tonks; Kazushi Mashima

doi:10.1021/jacs.8b13390

Bis(imido)vanadium(V)-Catalyzed [2+2+1] Coupling of Alkynes and Azobenzenes Giving Multisubstituted Pyrroles

Kento Kawakita, Evan P. Beaumier, Yuya Kakiuchi, Hayato Tsurugi, Ian A. Tonks, Kazushi Mashima

Chemistry (Twin Cities)

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Abstract

The combination of VCl ₃ (THF) ₃ and N,N-bis(trimethylsilyl)aniline (1a) is an efficient catalyst for the [2+2+1] coupling reaction of alkynes and azobenzenes, giving multisubstituted pyrroles. A plausible reaction mechanism involves the generation of a mono(imido)vanadium(III) species as an initiation step, where 1a served as an imido source with concomitant release of 2 equiv of ClSiMe ₃ , followed by a reaction with azobenzene to form a catalytically active bis(imido)vanadium(V) species via N=N bond cleavage.

Original language	English (US)
Pages (from-to)	4194-4198
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	141
Issue number	10
DOIs	https://doi.org/10.1021/jacs.8b13390
State	Published - Mar 13 2019

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© Copyright 2019 American Chemical Society.

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https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6460926

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title = "Bis(imido)vanadium(V)-Catalyzed [2+2+1] Coupling of Alkynes and Azobenzenes Giving Multisubstituted Pyrroles",

abstract = " The combination of VCl 3 (THF) 3 and N,N-bis(trimethylsilyl)aniline (1a) is an efficient catalyst for the [2+2+1] coupling reaction of alkynes and azobenzenes, giving multisubstituted pyrroles. A plausible reaction mechanism involves the generation of a mono(imido)vanadium(III) species as an initiation step, where 1a served as an imido source with concomitant release of 2 equiv of ClSiMe 3 , followed by a reaction with azobenzene to form a catalytically active bis(imido)vanadium(V) species via N=N bond cleavage.",

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AU - Kawakita, Kento

AU - Beaumier, Evan P.

AU - Kakiuchi, Yuya

AU - Tsurugi, Hayato

AU - Tonks, Ian A.

AU - Mashima, Kazushi

PY - 2019/3/13

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N2 - The combination of VCl 3 (THF) 3 and N,N-bis(trimethylsilyl)aniline (1a) is an efficient catalyst for the [2+2+1] coupling reaction of alkynes and azobenzenes, giving multisubstituted pyrroles. A plausible reaction mechanism involves the generation of a mono(imido)vanadium(III) species as an initiation step, where 1a served as an imido source with concomitant release of 2 equiv of ClSiMe 3 , followed by a reaction with azobenzene to form a catalytically active bis(imido)vanadium(V) species via N=N bond cleavage.

AB - The combination of VCl 3 (THF) 3 and N,N-bis(trimethylsilyl)aniline (1a) is an efficient catalyst for the [2+2+1] coupling reaction of alkynes and azobenzenes, giving multisubstituted pyrroles. A plausible reaction mechanism involves the generation of a mono(imido)vanadium(III) species as an initiation step, where 1a served as an imido source with concomitant release of 2 equiv of ClSiMe 3 , followed by a reaction with azobenzene to form a catalytically active bis(imido)vanadium(V) species via N=N bond cleavage.

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Bis(imido)vanadium(V)-Catalyzed [2+2+1] Coupling of Alkynes and Azobenzenes Giving Multisubstituted Pyrroles

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