Related Experiment Video
Updated: Jul 15, 2025
Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
Boron-Assisted Cobalt-Catalyzed C-H Methylation Using CO2 and H2
Qin Shi1,2, Haiyan Hu1,2, Minxing Du1
1State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, P. R. China.
Abstract:
C-H methylation of heteroarenes (e.g., indoles, pyrroles, etc.) is frequently applied in the synthesis of drug/biorelated compounds. We herein report the use of CO2/H2 as a methylation reagent for selective C-H methylation of indoles and pyrroles in the presence of cobalt/B(C6F5)3 cocatalysts. The Lewis acidic additive B(C6F5)3 is essential to achieving good reactivity for a broad scope of substituted indoles and pyrroles (20 examples, up to 92% yields). The C-H methylation is accomplished via the CO2 reduction/C-C bond formation/reduction sequence. Water is the only byproduct. This system based on the use of non-noble metal catalysts features an environmentally benign alternative for C-H methylation.
Related Concept Videos
03:08Hydroboration-Oxidation of Alkenes
02:36Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
02:15Preparation of Alcohols via Addition Reactions
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
01:33Carboxylic Acids to Methylesters: Alkylation using Diazomethane
02:47Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
02:23Alcohols from Carbonyl Compounds: Reduction
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...