Acyl Radicals from Benzothiazolines: Synthons for Alkylation, Alkenylation, and Alkynylation Reactions

Li, Lei; Guo, Shan; Wang, Qi; Zhu, Jin

doi:10.1021/acs.orglett.9b01717

Cited by 52 publications

(31 citation statements)

References 75 publications

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“…On the basis of above-described mechanistic experiments and previous literature reports [33][34][35][36][41][42][43], a plausible mechanism is proposed in Scheme 4d. Under blue LED irradiation, benzothiazoline reached its photoexcited state (1a*), a strong photoreductant (−1.68 V vs. SCE).…”

Section: Generating Informationmentioning

confidence: 78%

“…At the outset, C(2)-benzoyl-substituted benzothiazoline 1a was synthesized through a one-step condensation reaction of 2-aminothiophenol with 1,2-diphenylethanedione [41][42][43] to test the feasibility of our photochemical design. As shown in Figure 1a, the UV-vis absorption spectrum of 1a in CHCl 3 confirmed its ability to absorb in the visible frequency region, up to 475 nm.…”

Section: Photophysical Property Of Benzothiazolinesmentioning

confidence: 99%

“…In 2013, Tang et al found that C(2)-substituted benzothiazoline derivatives could serve as carbanion types of alkyl-transfer reagents under thermal reaction conditions [40]. Until 2019, the group of Zhu reported a photo-promoted radical alkylation, alkenylation, and alkynylation of olefins by using C(2)-substituted benzothiazolines as acyl radical precursors [41]. In this contribution, N-I bond homolysis of the in situ formed hypervalent iodine complex under visible light irradiation was proposed as the key step to acquiring the formation of acyl radicals.…”

Section: Introductionmentioning

confidence: 99%

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Direct Photoexcitation of Benzothiazolines: Acyl Radical Generation and Application to Access Heterocycles

Lü

et al. 2021

Molecules

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An acyl radical generation and functionalization strategy through direct photoexcitation of benzothiazolines has been developed. The formed acyl radical species can either be trapped by quinoxalin-2-ones to realize their C(3)-H functionalization or trigger a cascade radical cyclization with isonitriles to synthesise biologically important phenanthridines. The synthetic value of this protocol can be further illustrated by the modification of quinoxalin-2-ones, containing important natural products and drug-based complex molecules.

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Section: Generating Informationmentioning

confidence: 78%

Section: Photophysical Property Of Benzothiazolinesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Direct Photoexcitation of Benzothiazolines: Acyl Radical Generation and Application to Access Heterocycles

Lü

et al. 2021

Molecules

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“…Another example of photocatalytic, acyl radical alkenylation was recently reported recently by Zhu et al The authors used C2‐acyl‐substituted benzothiazolines as acyl radical precursors and 1,1‐dicyano‐1‐alkenes, in the presence of hypervalent iodine reagents to obtain β,β‐dicyanoenones in 50–80 % yield. Additionally, few examples involving acylation of alkynes, followed by subsequent cyclization, were reported …”

Section: C–c Bond: Sp2‐sp2 Disconnectionmentioning

confidence: 99%

A Retrosynthetic Approach for Photocatalysis

et al. 2020

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Visible‐light‐mediated chemical reactions have become very popular within the last 15 years. Many excellent reviews have summarized reaction principles and recent results in photochemistry and photocatalysis. However, despite their popularity photochemistry and photoredox catalysis are not regular parts of the bachelor and master curriculum of chemistry education. As a consequence, most chemists will use in synthesis planning classic retrosynthetic disconnections and only rarely consider photocatalytic steps. The aim of this article is to be a useful tool for synthetic chemists, that are interested in the synthetic aspects of photocatalysis and looking for a specific retrosynthetic disconnection. Not only are informative schemes provided but also are the availability of the catalysts and reagents as well as the functional group tolerance of the respective method briefly discussed.

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“…t-Butyl phenylcyanoacrylate was synthesized by condensation catalyzed by porous silicate quaternary ammonium composite materials [1]. It was involved in studies of synthons for alkylation, alkenylation, and alkynylation reactions of acyl radicals from benzothiazolines [2].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and styrene copolymerization of novel alkyl ring-substituted t-butyl phenylcyanoacrylates

Ibrahim

Abu-Alrob

Agoytia

et al. 2021

Preprint

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Novel alkyl ring-substituted t-butyl phenylcyanoacrylates, RPhCH=C(CN)CO2C(CH3)3 (where R is H, 2-methyl, 3-methyl, 4-methyl, 2-ethyl, 4-ethyl, 4-propyl, 4-i-propyl, 4-butyl, 4-i-butyl) were prepared and copolymerized with styrene. The acrylates were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and t-butyl cyanoacetate, and characterized by CHN analysis, IR, 1H and 13C NMR. All the ethylenes were copolymerized with styrene in solution with radical initiation (ABCN) at 70C. The compositions of the copolymers were calculated from nitrogen analysis.

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Acyl Radicals from Benzothiazolines: Synthons for Alkylation, Alkenylation, and Alkynylation Reactions

Cited by 52 publications

References 75 publications

Direct Photoexcitation of Benzothiazolines: Acyl Radical Generation and Application to Access Heterocycles

Direct Photoexcitation of Benzothiazolines: Acyl Radical Generation and Application to Access Heterocycles

A Retrosynthetic Approach for Photocatalysis

Synthesis and styrene copolymerization of novel alkyl ring-substituted t-butyl phenylcyanoacrylates

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