In real-world scenarios it may be an inconvenience to isolate and purify RAE coupling partners. In other cases, the RAE may be too hydrolytically labile to be easily isolated. Thus, an in situ protocol for RAE generation was developed as depicted in Table . The stable RAE precursor to 32 was used as a test case for this purpose. The only major procedural difference here involved conducting activation and cross coupling steps under a balloon of Ar. This was necessary due to the empirical observation that the presence of urea byproduct (from RAE formation) rendered the reaction more air-sensitive. This is likely due to the urea's ability to complex the nickel catalyst and interfere with productive cross coupling under air. Using this modified in situ protocol, 32 was obtained in 62% isolated yield (75% NMR yield). Substrates 33-37, unlike 32, utilized RAEs that were either unstable or difficult to purify. Due to the polar nature of products 33-37, NMR yields are also given as some material was lost during purification. RAE's bearing trifluoromethyl motifs were surprisingly hydrolytically labile. Fortunately, utilizing the in situ protocol, trisubstituted pyridine 33 could be accessed in 33% isolated yield (53% NMR yield). Next, a 3oxabicyclo [3.1.1]heptane bearing RAE could be coupled with 2-fluoro-4-bromo pyridine to afford 34 in 34% isolated yield. Sulfone bearing redox active esters were highly challenging to purify due to degradation on silica as well as coelution with coupling reagent byproducts. However, 35 was accessed efficiently in 43% isolated yield (52% NMR yield) after coupling with a densely functionalized bromoazaindole. RAE generated from amino acid derivatives and dipeptides were particularly challenging to purify when reactive residues were used but could be coupled efficiently using this protocol. Tryptophan analog 36, bearing an unprotected indole, was accessed in 31% isolated yield (46% NMR yield). Finally, a tyrosine bearing dipeptide was engaged in successful cross coupling, delivering 37 in 40% yield (45% NMR yield) in the presence of the unprotected phenol.