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1.
RhIII‐Catalyzed Hydroacylation Reactions between N‐Sulfonyl 2‐Aminobenzaldehydes and Olefins
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Tao Zhang Zisong Qi Xueyun Zhang Prof. Lamei Wu Prof. Dr. Xingwei Li 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(12):3283-3287
Metal‐catalyzed hydroacylation of olefins represents an important atom‐economic synthetic process in C?H activation. For the first time highly efficient RhIIICp*‐catalyzed hydroacylation was realized in the coupling of N‐sulfonyl 2‐aminobenzaldehydes with both conjugated and aliphatic olefins, leading to the synthesis of various aryl ketones. Occasionally, oxidative coupling occurred when a silver(I) oxidant was used. 相似文献
2.
Rhodium‐Catalyzed Annulative Coupling of 3‐Phenylthiophenes with Alkynes Involving Double C‐H Bond Cleavages
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Tomonori Iitsuka Dr. Koji Hirano Prof. Dr. Tetsuya Satoh Prof. Dr. Masahiro Miura 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(2):385-389
Double C?H bond activation took place efficiently upon treatment of 3‐phenylthiophenes with alkynes in the presence of a rhodium catalyst and a copper salt oxidant to form the corresponding naphthothiophene derivatives. Dehydrogenative coupling with alkenes was also found to occur on the phenyl moiety rather than the thiophene ring. These reactions provide straightforward synthetic methods for π‐conjugated molecules involving a thiophene unit from readily available, simple building blocks. 相似文献
3.
Dr. Yaxi Yang Dr. Wei Hou Lihuai Qin Dr. Juanjuan Du Huijin Feng Dr. Bing Zhou Dr. Yuanchao Li 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(2):416-420
The rhodium‐catalyzed intermolecular direct C?H thiolation of arenes with aryl and alkyl disulfides was developed for the first time to provide a convenient route to aryl thioethers. This strategy is compatible with many different directing groups and exhibits excellent functional group tolerance. More significantly, mono‐ or dithiolation can be selectively achieved, thus providing a straightforward way for selective preparation of aryl thioethers and dithioethers. 相似文献
4.
5.
Construction of Axial Chirality by Rhodium‐Catalyzed Asymmetric Dehydrogenative Heck Coupling of Biaryl Compounds with Alkenes
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Jun Zheng Prof. Dr. Shu‐Li You 《Angewandte Chemie (International ed. in English)》2014,53(48):13244-13247
Enantioselective construction of axially chiral biaryls by direct C? H bond functionalization reactions has been realized. Novel axially chiral biaryls were synthesized by the direct C? H bond olefination of biaryl compounds, using a chiral [Cp*RhIII] catalyst, in good to excellent yields and enantioselectivities. The obtained axially chiral biaryls were found as suitable ligands for rhodium‐catalyzed asymmetric conjugate additions. 相似文献
6.
Dr. Lanting Xu Chao Zhang Dr. Yupeng He Dr. Lushi Tan Prof. Dr. Dawei Ma 《Angewandte Chemie (International ed. in English)》2016,55(1):321-325
An efficient rhodium‐catalyzed method for direct C? H functionalization at the C7 position of a wide range of indoles has been developed. Good to excellent yields of alkenylation products were observed with acrylates, styrenes, and vinyl phenyl sulfones, whereas the saturated alkylation products were obtained in good yield with α,β‐unsaturated ketones. Both the N‐pivaloyl directing group and the rhodium catalyst proved to be crucial for high regioselectivity and conversion. 相似文献
7.
OH‐Directed Alkynylation of 2‐Vinylphenols with Ethynyl Benziodoxolones: A Fast Access to Terminal 1,3‐Enynes
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Peter Finkbeiner Ulrich Kloeckner Jun.‐Prof. Dr. Boris J. Nachtsheim 《Angewandte Chemie (International ed. in English)》2015,54(16):4949-4952
The first direct alkynylation of 2‐vinylphenols was developed. The rationally optimized hypervalent iodine reagent TIPS‐EBX* in combination with [(Cp*RhCl2)2] as a C? H‐activating transition metal catalyst enables the construction of a variety of highly substituted 1,3‐enynes in high yields of up to 98 %. This novel C? H activation method shows excellent chemoselectivity and exclusive (Z)‐stereoselectivity, and it is also remarkably mild and tolerates a variety of functional groups. Furthermore, synthetic modifications of the resulting 1,3‐enynes were demonstrated. To our knowledge, this is the first example for an OH‐directed C? H alkynylation with hypervalent iodine reagents. 相似文献
8.
Hydroarylations of Heterobicyclic Alkenes through Rhodium‐Catalyzed Directed CH Functionalizations of S‐Aryl Sulfoximines
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Dr. Wanrong Dong Dr. Kanniyappan Parthasarathy Ying Cheng Dr. Fangfang Pan Prof. Dr. Carsten Bolm 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(48):15732-15736
Rhodium‐catalyzed directed CH‐functionalizations have been used in hydroarylations of heterobicyclic alkenes with NH‐sulfoximines. Unexpectedly, the bicyclic framework is retained, resulting in the formation of addition products being attractive intermediates for functionalized molecules that are difficult to prepare by other means. 相似文献
9.
Zinc‐Catalyzed Dehydrogenative Cross‐Coupling of Terminal Alkynes with Aldehydes: Access to Ynones
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Shan Tang Li Zeng Yichang Liu Prof. Aiwen Lei 《Angewandte Chemie (International ed. in English)》2015,54(52):15850-15853
Because of the lack of redox ability, zinc has seldom been used as a catalyst in dehydrogenative cross‐coupling reactions. Herein, a novel zinc‐catalyzed dehydrogenative C(sp2)? H/C(sp)? H cross‐coupling of terminal alkynes with aldehydes was developed, and provides a simple way to access ynones from readily available materials under mild reaction conditions. Good reaction selectivity can be achieved with a 1:1 ratio of terminal alkyne and aldehyde. Various terminal alkynes and aldehydes are suitable in this transformation. 相似文献
10.
Rhodium‐Catalyzed Direct Amination of Arenes with Nitrosobenzenes: A New Route to Diarylamines
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Dr. Juanjuan Du Dr. Yaxi Yang Huijin Feng Dr. Yuanchao Li Dr. Bing Zhou 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(19):5727-5731
A RhIII‐catalyzed addition of aryl C?H bonds to nitrosobenzenes, followed by cleavage of the resulting hydroxylamines in situ, has been reported. Different directing groups, such as N‐based heterocycles and ketoximes, can be used in this C?H amination process, providing valuable diarylamines in excellent yields. Most importantly, this process provides a new method for attaching arylamine groups to aromatic rings. 相似文献
11.
Efficient Rhodium‐Catalyzed Multicomponent Reaction for the Synthesis of Novel Propargylamines
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Dr. Laura Rubio‐Pérez Dr. Manuel Iglesias Julen Munárriz Dr. Victor Polo Prof. Dr. Jesús J. Pérez‐Torrente Prof. Dr. Luis A. Oro 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(49):17701-17707
[{Rh(μ‐Cl)(H)2(IPr)}2] (IPr = 1,3‐bis‐(2,6‐diisopropylphenyl)imidazole‐2‐ylidene) was found to be an efficient catalyst for the synthesis of novel propargylamines by a one‐pot three‐component reaction between primary arylamines, aliphatic aldehydes, and triisopropylsilylacetylene. This methodology offers an efficient synthetic pathway for the preparation of secondary propargylamines derived from aliphatic aldehydes. The reactivity of [{Rh(μ‐Cl)(H)2(IPr)}2] with amines and aldehydes was studied, leading to the identification of complexes [RhCl(CO)IPr(MesNH2)] (MesNH2 = 2,4,6‐trimethylaniline) and [RhCl(CO)2IPr]. The latter shows a very low catalytic activity while the former brought about reaction rates similar to those obtained with [{Rh(μ‐Cl)(H)2(IPr)}2]. Besides, complex [RhCl(CO)IPr(MesNH2)] reacts with an excess of amine and aldehyde to give [RhCl(CO)IPr{MesN?CHCH2CH(CH3)2}], which was postulated as the active species. A mechanism that clarifies the scarcely studied catalytic cycle of A3‐coupling reactions is proposed based on reactivity studies and DFT calculations. 相似文献
12.
Rhodium‐Catalyzed CS and CN Functionalization of Arenes: Combination of CH Activation and Hypervalent Iodine Chemistry
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Fen Wang Xinzhang Yu Zisong Qi Prof. Dr. Xingwei Li 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(2):511-516
Rhodium‐catalyzed sulfonylation, thioetherification, thiocyanation, and other heterofunctionalizations of arenes bearing a heterocyclic directing group have been realized. The reaction proceeds by initial RhIII‐catalyzed C?H hyperiodination of arene at room temperature followed by uncatalyzed nucleophilic functionalization. A diaryliodonium salt is isolated as an intermediate, which represents umpolung of the arene substrate, in contrast to previous studies that suggested umpolung of the coupling partner. 相似文献
13.
Synthesis of Spirocyclic Enones by Rhodium‐Catalyzed Dearomatizing Oxidative Annulation of 2‐Alkenylphenols with Alkynes and Enynes
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Szymon Kujawa Dr. Daniel Best Dr. David J. Burns Prof. Hon Wai Lam 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(28):8599-8602
The dearomatizing oxidative annulation of 2‐alkenylphenols with alkynes and enynes proceeds with high yields and regioselectivities under RhIII catalysis. These reactions are successful using Cu(OAc)2 or air as the stoichiometric oxidant, and provide spirocyclic enones, the basic ring system of which appears in several natural products. Application of this process to the preparation of a highly functionalized tetracycle is also demonstrated. 相似文献
14.
Rhodium‐Catalyzed CH Annulation of Nitrones with Alkynes: A Regiospecific Route to Unsymmetrical 2,3‐Diaryl‐Substituted Indoles
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Hao Yan Dr. Haolong Wang Dr. Xincheng Li Dr. Xiaoyi Xin Dr. Chunxiang Wang Prof. Dr. Boshun Wan 《Angewandte Chemie (International ed. in English)》2015,54(36):10613-10617
The direct C? H annulation of anilines or related compounds with internal alkynes provides straightforward access to 2,3‐disubstituted indole products. However, this transformation proceeds with poor regioselectivity in the synthesis of unsymmetrically 2,3‐diaryl substituted indoles. Herein, we report the rhodium(III)‐catalyzed C? H annulation of nitrones with symmetrical diaryl alkynes as an alternative method to prepare 2,3‐diaryl‐substituted N‐unprotected indoles with two different aryl groups. One of the aryl substituents is derived from N?C‐aryl ring of the nitrone and the other from the alkyne substrate, thus providing the indole products with exclusive regioselectivity. 相似文献
15.
Chao Feng Prof. Dr. Teck‐Peng Loh 《Angewandte Chemie (International ed. in English)》2014,53(10):2722-2726
The rhodium(III)‐catalyzed ortho C? H alkynylation of non‐electronically activated arenes is disclosed. This process features a straightforward and highly effective protocol for the synthesis of functionalized alkynes and represents the first example of merging a hypervalent iodine reagent with rhodium(III) catalysis. Notably, this reaction proceeds at room temperature, tolerates a variety of functional groups, and more importantly, exhibits high selectivity for monoalkynylation. 相似文献
16.
Wen‐Hao Guo Qiao‐Qiao Min Ji‐Wei Gu Prof. Dr. Xingang Zhang 《Angewandte Chemie (International ed. in English)》2015,54(31):9075-9078
An ortho‐selective C? F bond borylation between N‐heterocycle‐substituted polyfluoroarenes and Bpin‐Bpin with simple and commercially available [Rh(cod)2]BF4 as a catalyst is now reported. The reaction proceeds under mild reaction conditions with high efficiency and broad substrate scope, even toward monofluoroarene, thus providing a facile access to a wide range of borylated fluoroarenes that are useful for photoelectronic materials. Preliminary mechanistic studies reveal that a RhIII/V catalytic cycle via a key intermediate rhodium(III) hydride complex [(H)RhIIILn(Bpin)] may be involved in the reaction. 相似文献
17.
Rhodium(III)‐Catalyzed Three‐Component Reaction of Imines,Alkynes, and Aldehydes through CH Activation
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Ji‐Rong Huang Qiang Song Yu‐Qin Zhu Liu Qin Prof. Dr. Zhi‐Yong Qian Prof. Dr. Lin Dong 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(51):16882-16886
An efficient rhodium(III)‐catalyzed tandem three‐component reaction of imines, alkynes and aldehydes through C?H activation has been developed. High stereo‐ and regioselectivity, as well as good yields were obtained in most cases. The simple and atom‐economical approach offers a broad scope of substrates, providing polycyclic skeletons with potential biological properties. 相似文献
18.
Aerobic Asymmetric Dehydrogenative Cross‐Coupling between Two CH Groups Catalyzed by a Chiral‐at‐Metal Rhodium Complex
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Yuqi Tan Wei Yuan Dr. Lei Gong Prof. Dr. Eric Meggers 《Angewandte Chemie (International ed. in English)》2015,54(44):13045-13048
A sustainable C? C bond formation is merged with the catalytic asymmetric generation of one or two stereocenters. The introduced catalytic asymmetric cross‐coupling of two C? H groups with molecular oxygen as the oxidant profits from the oxidative robustness of a chiral‐at‐metal rhodium(III) catalyst and exploits an autoxidation mechanism or visible‐light photosensitized oxidation. In the latter case, the catalyst serves a dual function, namely as a chiral Lewis acid for catalyzing enantioselective enolate chemistry and at the same time as a visible‐light‐driven photoredox catalyst. 相似文献
19.
Diastereoselective Carbocyclization of 1,6‐Heptadienes Triggered by Rhodium‐Catalyzed Activation of an Olefinic CH Bond
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Dr. Christophe Aïssa Kelvin Y. T. Ho Dr. Daniel J. Tetlow María Pin‐Nó 《Angewandte Chemie (International ed. in English)》2014,53(16):4209-4212
The use of α,ω‐dienes as functionalization reagents for olefinic carbon–hydrogen bonds has been rarely studied. Reported herein is the rhodium(I)‐catalyzed rearrangement of prochiral 1,6‐heptadienes into [2,2,1]‐cycloheptane derivatives with concomitant creation of at least three stereogenic centers and complete diastereocontrol. Deuterium‐labeling studies and the isolation of a key intermediate are consistent with a group‐directed C? H bond activation, followed by two consecutive migratory insertions, with only the latter step being diastereoselective. 相似文献
20.
Rhodium‐Catalyzed Cyclization of Diynes with Nitrones: A Formal [2+2+5] Approach to Bridged Eight‐Membered Heterocycles
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Dr. Chunxiang Wang Dr. Dongping Wang Hao Yan Dr. Haolong Wang Dr. Bin Pan Dr. Xiaoyi Xin Dr. Xincheng Li Fan Wu Prof. Dr. Boshun Wan 《Angewandte Chemie (International ed. in English)》2014,53(44):11940-11943
N‐aryl‐substituted nitrones were employed as five‐atom coupling partners in the rhodium‐catalyzed cyclization with diynes. In this reaction, the nitrone moiety served as a directing group for the catalytic C? H activation of the N‐aryl ring. This formal [2+2+5] approach allows rapid access to bridged eight‐membered heterocycles with broad substrate scope. The results of this study may provide new insight into the chemistry of nitrones and find applications in the synthesis of other heterocycles. 相似文献