Beyond FLP additions: FLP deprotonation and C-O bond cleavage of aliphatic, aryl and ester derived olefins
Goraya, Armaan; Ajithkumar, V. S.; Ruhlandt, Karin; Stephan, Douglas W.; McCahill, Jenny SJ; Bedi, Vaibhav; Chemical Communications  (2026) –; doi:10.1039/D6CC00412A

data_7135372
_publ_section_title
;
 Beyond FLP additions: FLP deprotonation and C-O bond cleavage of
 aliphatic, aryl and ester derived olefins.
;
_journal_issue                   19
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5531
_journal_page_last               5535
_journal_paper_doi               10.1039/d6cc00412a
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C12 H28 P, C42 H9 B2 F30 O2, C H2 Cl2'
_chemical_formula_sum            'C55 H39 B2 Cl2 F30 O2 P'
_chemical_formula_weight         1425.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2025-10-21
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2026-01-11 deposited with the CCDC.	2026-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                81.710(2)
_cell_angle_beta                 81.998(2)
_cell_angle_gamma                88.438(2)
_cell_formula_units_Z            2
_cell_length_a                   12.5198(8)
_cell_length_b                   12.5678(9)
_cell_length_c                   18.6747(13)
_cell_measurement_reflns_used    9631
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.500
_cell_measurement_theta_min      2.328
_cell_volume                     2879.3(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.01
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            92586
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.858
_diffrn_reflns_theta_min         2.225
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.7098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0483 before and 0.0424 after correction.
The Ratio of minimum to maximum transmission is 0.9517.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_description       block
_exptl_crystal_F_000             1428
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     861
_refine_ls_number_reflns         14966
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0452P)^2^+1.1222P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1020
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11869
_reflns_number_total             14966
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc00412a2.cif
_cod_data_source_block           ag_internallolefin_0ma_a
_cod_depositor_comments
'Adding full bibliography for 7135371--7135375.cif.'
_cod_database_code               7135372
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: Cl2(0.75) C2(0.75) H2A(0.75) H2B(0.75) Cl3(0.25) C3(0.25)
 H3A(0.25) H3B(0.25)
3.a Secondary CH2 refined with riding coordinates:
 C01O(H01A,H01B), C023(H02A,H02B), C2(H2A,H2B), C3(H3A,H3B)
3.b Aromatic/amide H refined with riding coordinates:
 C013(H013), C014(H014)
3.c Idealised Me refined as rotating group:
 C01R(H01C,H01D,H01E), C028(H02F,H02G,H02H), C02A(H02I,H02J,H02K), C02B(H02L,
 H02M,H02N), C02C(H02O,H02P,H02Q), C02D(H02R,H02S,H02T), C02E(H02U,H02V,H02W),
 C02G(H02X,H02Y,H), C02I(H02Z,HA,HB), C02J(H02C,H02D,H02E)
;
_shelx_res_checksum              1590
_olex2_submission_special_instructions 'No special instructions were received'