Table 4.

TON, TOF, and PMI values of optimized HCS.^[a]

Entry	2	1 [equiv.]	Ligand [mol %]	CuI [mol %]	T [°C]	t [h]	Cycles	Overall yield[b] [%]	TON[c]	TOF[c] [h−1]	PMI	PMI[d] with recovery
1	2 a	1.05	TPPTS (0.6)	0.05	30	3	5	95	2375	158	7.3	2.9
2	2 a	1.05	TPPTS (0.4)	–	60	3	4	93	1860	155	7.6	3.0
3	2 b	1.2	sSPhos (0.6)	0.05	60	4	3	90	1380	112	7.9	3.0
4	2 c	1.2	sSPhos (0.6)	–	60	4	4	88	1760	110	8.2	3.4

[a] All reactions were carried out under a nitrogen atmosphere with a 2.5 m concentration; the conversions were measured by HPLC at the end of each cycle, being always higher than 90 %. [b] The yield was obtained combining all the crude extracts. The reaction could be also performed by recycling the distilled cyclohexane in the following extraction process; however, this option was not used for PMI calculation. [c] TON and TOF were calculated considering the average yield and the overall reaction time. [d] PMI was recalculated after recovery of cyclohexane (95 %), TMG (95 %), HEP (95 %), and palladium (90 %), see the Supporting Information for the detailed calculation.