Top JACS papers of 2012 “most downloaded over 12 months”

Simon Lang

Problem Set

1/25/13

A New Method For Direct Difluoromethylation- Phil Baran JACS 2012 1494

• No prefunctionalization- direct transfer

Mechanism?

DFMS = [Zn](SO2CF2H)2

TFA/solvent not used for mechanism Assume trace metal activates peroxide

Mechanism?

PNAS 2011 14411-14415

Rationalize these results

(+)-Scholarisine A- Amos Smith III JACS 2012 4037

20 steps from known

Provide the product

Reductive Cyclization

Rxn name?

Draw/talk through what happens?

Benzoyl Chloride DMP

Intermolecular Ritter-Type C-H Amination of Unactivated sp3 Carbons

• Phil Baran JACS 2547 2012

Inspiration

Reagent name??

Mechanism?? Think: Selectfluor = electrophillic F and Ritter rxn

R. Eric Banks, Chem Comm 1996 1629.

Nature-Inspired Total Synthesis of (-) Fusarisetin A

Emmanuel A. Theodorakis JACS 2012 5072 Nine steps from commercially available (S)-(-)-citronellal $20/g

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Via

End Game

Mechanism???