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. Author manuscript; available in PMC: 2018 Jun 28.
Published in final edited form as: J Am Chem Soc. 2017 Jun 14;139(25):8710–8717. doi: 10.1021/jacs.7b04149

Table 5.

Three-Component Coupling of Linchpin 19 via ARC/CCR

graphic file with name nihms890189u6.jpg
nucleophile electrophile R5 R6 yield
n-BuLi graphic file with name nihms890189t10.jpg n-Bu graphic file with name nihms890189t11.jpg 25a 49%a (53%)b
n-BuLi graphic file with name nihms890189t12.jpg n-Bu graphic file with name nihms890189t13.jpg 25b 61%a (57%)b
n-BuLi graphic file with name nihms890189t14.jpg n-Bu graphic file with name nihms890189t15.jpg 25c 54%a (59%)b
n-BuLi graphic file with name nihms890189t16.jpg n-Bu graphic file with name nihms890189t17.jpg 25d 55%a (62%)b
n-BuLi graphic file with name nihms890189t26.jpg n-Bu graphic file with name nihms890189t17.jpg 25e (55%)b
n-BuLi graphic file with name nihms890189t18.jpg n-Bu graphic file with name nihms890189t19.jpg 25f (68%)b
MeLi graphic file with name nihms890189t14.jpg Me graphic file with name nihms890189t15.jpg 25g 55%a (51%)b
PhLi graphic file with name nihms890189t14.jpg Ph graphic file with name nihms890189t15.jpg 25h 63%a (52%)b
a

Conditions 1: (a) 2.0 equiv of nucleophile, THF, −78 °C; (b) 2.0 equiv of CuBr·DMS, HMPA/THF (1:1), 60 °C; then (c) and (d).

b

Conditions 2: (a) 1.1 equiv of nucleophile, THF, −78 °C; (b) 2.0 equiv of CuBr·DMS, 1.0 equiv of t-BuOK, HMPA, 60 °C; then (c) and (d).