Direct olefination of benzaldehydes into 1,3-diarylpropenes <i>via</i> a copper-catalyzed heterodomino Knoevenagel-decarboxylation-Csp<sup>3</sup>-H activation sequence

Zhao, Yingwei; Sun, Lu; Zeng, Tieqiang; Wang, Jiayi; Peng, Yanqing; Song, Gonghua

doi:10.1039/c4ob00155a

Cited by 9 publications

(4 citation statements)

References 53 publications

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“…同一课题组 [64] 后来还报道了铁和 DTBP 催化甲基芳烃与肉桂酸的反应. 随后, Song 等 [65] 报道了另一种反应变体, 该反应从醛开始, 通过使用铜和 DTBP 催化原位生成的肉桂酸与甲苯脱羧偶联. 图式 36 肉桂酸与甲苯衍生物的烯烃化反应 Scheme 36 Olefination of cinnamic acids with toluene derivatives 2015 年, 黄汉民等 [66] 开发了一种新型的铜(II)催化、区域选择性的烯酮与甲基芳烃 α-苄基化反应(Scheme 37).…”

Section: C(sp 3 )-H 键烯烃化反应unclassified

Recent Progress in Benzylic C(sp³)—H Functionalization of Toluene and Its Derivatives

Cai¹,

Dong²

2022

Chinese Journal of Organic Chemistry

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Toluene derivatives are alkyl aromatic hydrocarbons derived from oil and natural gas and are among the cheapest and most readily available materials for the chemical industry. C-H functionalization is important for the synthesis of various bioactive substances, and inert benzylic hydrocarbon bond activation has long been a big challenge in this field due to the high hydrocarbon bond energy. Therefore, the development of simple and efficient methods for C-C and C-X bonds formation has been demonstrated as one of the hot topics by activating the benzylic C(sp 3 )-H bonds in recent years. The progress in benzylic C(sp 3 )-H functionalization of toluene and its derivatives under different catalytic conditions in the past decade is summarized according to different reaction classifications. The reaction substrate compatibility, mechanism, applications, advantages and limitations in this field are also discussed in detail. Keywords toluene; C(sp 3 )-H bond activation; inert; selective catalysis; C-X bonds formation 碳氢键在有机化合物中极为普遍, 开发将碳氢键选择性转化为碳碳键或碳杂键的有效方法是有机化学中一个重大挑战 [1] . 过去的几十年里, C(sp 3 )-H 键催化活化被广泛用于各类新化学键的构建, 这类构建转化在化学科学中得到广泛的应用, 包括药物、天然产物、农用化学品和聚合物的合成等 [2] . 因此, 通过碳氢化合物的难点之一 [3] . 一些常见的含 C(sp 3 )-H 键的化合物以及 pK a 值 [4] 如图 1 所示, 我们课题组前期对二芳基甲烷苄位 C(sp 3

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Section: C(sp 3 )-H 键烯烃化反应unclassified

Recent Progress in Benzylic C(sp³)—H Functionalization of Toluene and Its Derivatives

Cai¹,

Dong²

2022

Chinese Journal of Organic Chemistry

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“…(E)-1-Methoxy-4-(3-(p-tolyl)prop-1-en-1-yl)benzene (3i). 21 Elution with EtOAc/petroleum ether 1/150 (v/v), white solid, yield 114.5 mg (96%). 1 H NMR (400 MHz, CDCl 3 ): δ 7.27 (dd, J = 8.7, 2.0 Hz, 2H), 7.11 (s, 4H), 6.82 (dd, J = 8.8, 2.1 Hz, 2H), 6.38 (d, J = 15.8 Hz, 1H), 6.26−6.12 (m, 1H), 3.78 (s, 3H), 3.48 (d, J = 6.8 Hz, 2H), 2.32 (s, 3H).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Nickel-Catalyzed Cross-Coupling of Allyl Alcohols with Aryl- or Alkenylzinc Reagents

Yang

Wang

2016

J. Org. Chem.

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Nickel-catalyzed cross-coupling of allyl alcohols with aryl- and alkenylzinc chlorides through C-O bond cleavage was performed. Reaction of (E)-3-phenylprop-2-en-1-ol and 1-aryl-prop-2-en-1-ols with aryl- or alkenylzinc chlorides gave linear cross-coupling products. Reaction of 1-phenyl- or 1-methyl-substituted (E)-3-phenylprop-2-en-1-ol with aryl- or alkenylzinc chlorides resulted in 3-aryl/alkenyl-substituted (E)-(prop-1-ene-1,3-diyl)dibenzenes or 3-aryl/alkenyl-substituted (E)-(but-1-enyl)benzene. Reaction of allyl alcohol with p-MeNCHZnCl resulted in a mixture of normal coupling product 4-allyl-N,N-dimethylaniline and its isomerized product N,N-dimethyl-4-(prop-1-en-1-yl)aniline.

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“…75 Song et al reported another variation of the reaction starting from aldehydes via in situ generated cinnamic acids using copper and DTBP catalysis. 76 Li et al achieved the synthesis of functionalised oxindoles from methylarenes and acrylamides using IrCl 3 and DTBP (Scheme 53). 77 Several substituents on both the coupling partners participated in the reaction; polymethylated arenes selectively participate in the reaction.…”

Section: Synthesis Of Carbamates Thioamides and Esters Our Group Has ...mentioning

confidence: 99%

Utilization of methylarenes as versatile building blocks in organic synthesis

2015

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The development of practical and efficient methods for C-C and C-X bond formation has attracted a great deal of current attention with the advent of C-H functionalization reactions. Hydrocarbons are perhaps the most inexpensive and readily available materials, and utilisation of such materials for the synthesis of essential chemicals is virtually and economically pragmatic. The means to utilize easily accessible hydrocarbons not only represents a useful, potent and straightforward alternative, but also constitutes an excellent opportunity to improve our chemical knowledge about a relatively unexplored domain. Early examples using alkylarenes are generally limited to their conversion to aldehydes, carboxylic acids, and nitriles. This review intends to focus on the latest developments adopting modern strategies for sp(3) C-H functionalization of methylarenes to achieve a diverse range of important organic compounds.

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Direct olefination of benzaldehydes into 1,3-diarylpropenes via a copper-catalyzed heterodomino Knoevenagel-decarboxylation-Csp³-H activation sequence

Abstract: Copper-catalyzed direct olefination of benzaldehydes into 1,3-diarylpropenes by a novel domino Knoevenagel-decarboxylation-Csp(3)-H activation sequence is reported. This method provides a concise and effective route toward the synthesis of unsymmetrical 1,3-diarylpropene derivatives.

Cited by 9 publications

References 53 publications

Recent Progress in Benzylic C(sp³)—H Functionalization of Toluene and Its Derivatives

Recent Progress in Benzylic C(sp³)—H Functionalization of Toluene and Its Derivatives

Nickel-Catalyzed Cross-Coupling of Allyl Alcohols with Aryl- or Alkenylzinc Reagents

Utilization of methylarenes as versatile building blocks in organic synthesis

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Direct olefination of benzaldehydes into 1,3-diarylpropenes via a copper-catalyzed heterodomino Knoevenagel-decarboxylation-Csp3-H activation sequence

Abstract: Copper-catalyzed direct olefination of benzaldehydes into 1,3-diarylpropenes by a novel domino Knoevenagel-decarboxylation-Csp(3)-H activation sequence is reported. This method provides a concise and effective route toward the synthesis of unsymmetrical 1,3-diarylpropene derivatives.

Cited by 9 publications

References 53 publications

Recent Progress in Benzylic C(sp3)—H Functionalization of Toluene and Its Derivatives

Recent Progress in Benzylic C(sp3)—H Functionalization of Toluene and Its Derivatives

Nickel-Catalyzed Cross-Coupling of Allyl Alcohols with Aryl- or Alkenylzinc Reagents

Utilization of methylarenes as versatile building blocks in organic synthesis

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Direct olefination of benzaldehydes into 1,3-diarylpropenes via a copper-catalyzed heterodomino Knoevenagel-decarboxylation-Csp³-H activation sequence

Recent Progress in Benzylic C(sp³)—H Functionalization of Toluene and Its Derivatives

Recent Progress in Benzylic C(sp³)—H Functionalization of Toluene and Its Derivatives