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Rhodium-Catalyzed C-H Activation/Annulation of N‑Chlorobenzamide Derivatives with Alkynes
Qing-Xin Jiang1,2, Ji-Chen Huang2, Teng-Bo Zhao2
1College of Chemistry and Chemical Engineering, Donghua University, 2399 Guangfulin Lu, Shanghai 201620, China.
None:
Highly efficient synthesis of isoquinolones is achieved by a Rh-(III)-catalyzed C-H activation/annulation of N-chlorobenzamide derivatives with alkynes. This transformation leverages the N-Cl moiety as a highly effective internal oxidant, enabling the reaction to proceed smoothly under mild conditions and delivering the target products in excellent yields (up to 98% yield). Control experiments further reveal the superior oxidizing ability of the N-Cl benzamide relative to its N-OMe and N-OPiv analogues. Notably, the reaction proceeds with 85% yield even at an exceptionally low catalyst loading of 0.05 mol %.
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02:24Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
02:35Electrophilic Addition to Alkynes: Hydrohalogenation
02:38Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
02:34Preparation of Alkynes: Dehydrohalogenation
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
02:27Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
02:17Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...