- Rhodium-catalyzed carbonylative coupling of alkyl halides with thiols: a radical process faster than easier nucleophilic substitution
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How to make a carbonylative coupling faster than the easier nucleophilic substitution? In this communication, a rhodium-catalyzed radical-based carbonylative coupling of alkyl halides with thiolphenols has been realized. Thioesters were isolated in good y
- Ai, Han-Jun,Rabeah, Jabor,Brückner, Angelika,Wu, Xiao-Feng
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supporting information
p. 1466 - 1469
(2021/02/21)
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- Copper-Catalyzed Regioselective Borocarbonylative Coupling of Unactivated Alkenes with Alkyl Halides: Synthesis of β-Boryl Ketones
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The borocarbonylative coupling of unactivated alkenes with alkyl halides remains a challenge. In this communication, a Cu-catalyzed borocarbonylative coupling of unactivated alkenes with alkyl halides for the synthesis of β-boryl ketones has been developed. A broad range of β-boryl ketone derivatives was prepared in moderate to excellent yields with complete regioselectivity.
- Wu, Fu-Peng,Yuan, Yang,Schünemann, Claas,Kamer, Paul C. J.,Wu, Xiao-Feng
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supporting information
p. 10451 - 10455
(2020/05/08)
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- IRAK DEGRADERS AND USES THEREOF
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The present invention provides compounds, compositions thereof, and methods of using the same.
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- Alkyl Carbagermatranes Enable Practical Palladium-Catalyzed sp2-sp3 Cross-Coupling
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Pd-catalyzed cross-coupling reactions have achieved tremendous accomplishments in the past decades. However, C(sp3)-hybridized nucleophiles generally remain as challenging coupling partners due to their sluggish transmetalation compared to the C(sp2)-hybridized counterparts. While a single-electron-transfer-based strategy using C(sp3)-hybridized nucleophiles had made significant progress recently, fewer breakthroughs have been made concerning the traditional two-electron mechanism involving C(sp3)-hybridized nucleophiles. In this report, we present a series of unique alkyl carbagermatranes that were proven to be highly reactive in cross-coupling reactions with our newly developed electron-deficient phosphine ligands. Generally, secondary alkyl carbagermatranes show slightly lower, yet comparable activity to its Sn analogue. Meanwhile, primary alkyl carbagermatranes exhibit high activity, and they were also proved stable enough to be compatible with various reactions. Chiral secondary benzyl carbagermatrane gave the coupling product under base/additive-free conditions with its configuration fully inversed, suggesting that transmetalation was carried out in an "SE2(open) Inv" pathway, which is consistent with Hiyama's previous observation. Notably, the cross-coupling of primary alkyl carbagermatranes could be performed under base/additive-free conditions with excellent functional group tolerance and therefore may have potentially important applications such as stapled peptide synthesis.
- Xu, Meng-Yu,Jiang, Wei-Tao,Li, Ying,Xu, Qing-Hao,Zhou, Qiao-Lan,Yang, Shuo,Xiao, Bin
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supporting information
p. 7582 - 7588
(2019/05/16)
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- Palladium-catalyzed C-H alkylation of 2-phenylpyridines with alkyl iodides
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Palladium-catalyzed C-H alkylation reaction of 2-phenylpyridines with alkyl iodides has been successfully developed. The palladacycles obtained from 2-phenylpyridines should act as the key intermediates in the alkylation reaction.
- Wang, Xiaoling,Ji, Xiaoming,Shao, Changdong,Zhang, Yu,Zhang, Yanghui
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supporting information
p. 5616 - 5624
(2017/07/12)
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- Enantioselective synthesis of (R)- and (S)-3-methylspermidines
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Earlier unknown enantiomerically pure (R)- and (S)-1,8-diamino-3-methyl-4-azaoctane's (3-MeSpd's) were synthesized within 11 steps with high overall yields and optical purity starting from commercially available R- and S-isomers of N-Boc-2-aminopropanol-1
- Khomutov,Keinanen,Hyvonen,Weisell,Vepsalainen,Alhonen,Kochetkov,Khomutov
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p. 548 - 553
(2015/10/12)
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- Reagents for lysergic acid diethylamide immunoassay
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The present invention provides hapten derivatives that are useful for the preparation of antigens, antibodies and reagents having superior performance characteristics for use in immunoassays for the detection of LSD and nor-LSD. In the present invention the LSD nucleus is derivatized out of the indole nitrogen to form an aminoalkyl derivative. Derivatives have also been synthesized out of the piperidine nitrogen of the LSD nucleus. The resulting haptens can then be further modified at these functionalized positions for linking to appropriate antigenic or labelling groups to provide reagents for LSD immunoassays having excellent sensitivity and selectivity for both LSD and nor-LSD.
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- Reductive cyclization of N-iodoalkyl cyclic imides to nitrogen-fused polycyclic amides induced by samarium diiodide
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SmI2-promoted cyclizations of cyclic imides having 3-iodopropyl or 4-iodobutyl groups on the imide nitrogen have been studied for construction of nitrogen-fused polycyclic amides.
- Ha, Deok-Chan,Yun, Chang-Soo,Yu, Eunsun
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p. 2577 - 2580
(2007/10/03)
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- AMINOALKYL AND RELATED SUBSTITUTED PHOSPHINIC ACID ANGIOTENSIN CONVERTING ENZYME INHIBITORS
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Compounds of the structure STR1 are provided which are inhibitors of angiotensin converting enzyme and are useful in the treatment of hypertension.
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- Biosynthesis of streptothricin F. 5. Formation of β-lysine by Streptomyces L-1689-23
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The formation of the β-lysine moiety of streptothricin F has been studied by feeding to Streptomyces L-1689-23 α-[3-13C,15N]-, α-[(3RS)-2H2]-, α-[(3R)-2H]-, and α[(3S)-2H]lysine and β-[(2S)-2H]lysine. From the analysis of either the 13C NMR or 2H NMR spectrum of the derived antibiotics, it has been determined that the α-nitrogen migrates to C-3 with inversion of configuration by an intramolecular process, and the 3-pro-R hydrogen migrates to C-2 with inversion of configuration by a process that is substantially or completely intermolecular. The very high degree of incorporation of labeled β-lysine indicates it is probably an intermediate in the biosynthesis of streptothricin F. The formation of the beta -lysine moiety of streptothricin F has been studied by feeding to Streptomyces L-1689-23 alpha - left bracket 3-**1**3C, **1**5N right bracket -, alpha - left bracket (3RS)-**2H//2 right bracket -, alpha - left bracket (3R)-**2H right bracket -, and alpha - left bracket (3S)-**2H right bracket lysine and beta - left bracket (2S)-**2H right bracket lysine. From the analysis of either the **1**3C NMR or **2H NMR spectrum of the derived antibotics, it has been determined that the alpha -nitrogen migrates to C-3 with inversion of configuration by an intramolecular process, and the 3-pro-R hydrogen migrates to C-2 with inversion of configuration by a process that is substantially or completely intermolecular. The very high degree of incorporation of labeled beta -lysine indicates it is probably an intermediate in the biosynthesis of streptothricin F.
- Thiruvengadam,Gould,Aberhart,Horng Jau Lin
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p. 5470 - 5476
(2007/10/08)
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