Useful Protocols

• General and reliable initiation for Grignard reagent preparation

• Facile preparation of ArZnX in MeCN (no RLi or RMgX needed)

• Acid activation of Zn powder
  (good for Reformatsky, ArZnX prep above) , lasts ages if stored under N2 in dessicator

• Stahl-Hoover oxidation (alcohol to aldehyde or ketone)
  honestly a modern standard for extremely broadly useful reactions. Use in places you might’ve otherwise opted for DMP or PCC

• Friedel-Crafts arene halogenation without FeX3/AlX3
  Update for electon-poor arenes

• Preparing a-substituted acrylates via Trost umpolung
  Just a really good reaction. Works with lots of protected N-equivalents, N-heterocycles, and tolerates a bunch of different types of propiolates

• Prep and user guide for SmI2 generation

• Guide on proper usage of AcrosSeal bottles and Lithiation/Borylation from the Aggarwal group

• General Use Mizoroki-Heck Conditions
  Gives a great starting point for Heck conditions that works with huge range of partners. Even if it’s not perfect, you’ll get some product to start.

• Preparation of Karstedt’s catalyst (hydrosilylation)

• Mild Nitro Reduction with Cu + Borohydride

• Sulfide to Sulfone oxidation with Sodium Tungstate / H2O2
  We use this one quite a bit. Works really well even with electron poor sulfides. Just be cautious with quenching the aqueous layer. Cooling with ice and slow addition of sodium thiosulfate solution are musts.

• Hydroxylation of Aryl Halides - Ullman-Ma
  This prep is excellent, extremely easy to set up and the ligands preps are a great first set of reactions for new trainees!

Useful reagents/groups

• 4-cyanobenzenesulfonyl protecting group
  (same deprotection as Ns, but no nitro issues)

• NaDA (sodium diisopropylamide) see pg 15 of SI

• Aryl zinc pivalates as convenient nucleophilic reagents‍ ‍(1)‍ ‍

• Tces (trichloroethoxysulfonyl) protecting group for amines and N-heterocycles
  Prep of TcesCl (see SI pg S22)‍ ‍
  Removal w/ Zn/AcOH (see also: Troc)

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Useful data tables

• Compilation of ground and excited state redox properties and triplet energies of photocatalysts (Teets)

• Redox potentials of carbanions and BDEs

• Redox potentials of common carbon-centered radicals

Resource Links

• NMR Solvent Peak Locations

• TLC Solvent Strength translator
  Tool to let you figure out if mixtures of different solvents are of comparable polarity (ex. What % Et2O in hexane ~~ 10% EtOAc in hexane)

• Bond-Dissociation Energy estimator
  Input SMILES of structure, get out BDEs for the bonds

• Photocatalyst Data Reference - Teets
  One of the most comprehensive all-in-one references for things like potentials, triplet energies, and lifetimes.

• Compilation of huge array of resources for chemists